Intermediates to prepare herbicidal pyrimidone derivatives

ABSTRACT

Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof, 
     
       
         
         
             
             
         
       
         
         
           
             X is CH or N; 
             Y is C(O) or S(O) 2 ; provided that when Y is S(O) 2 , then X is CH; 
             A is a radical selected from the group consisting of 
           
         
       
    
     
       
         
         
             
             
         
       
     
     and B 1 , B 2 , B 3 , T, R 1 , R 2  R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12  and R 13  are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling undesired vegetation comprising contacting the undesired vegetation or its environment with an effective amount of a compound or a composition of the invention.

FIELD OF THE INVENTION

This invention relates to certain bis-nitrogen heterocycles, their salts and compositions, and methods of their use for controlling undesirable vegetation. This invention also relates to certain intermediates and a method useful for preparing these bis-nitrogen heterocycles and their salts. This invention also relates to certain bis-nitrogen oxo or sulfono heterocycles, their salts and compositions, and methods of their use for controlling undesirable vegetation.

BACKGROUND OF THE INVENTION

The control of undesired vegetation is extremely important in achieving high crop efficiency. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, maize, potato, wheat, barley, tomato and plantation crops, among others, is very desirable. Unchecked weed growth in such useful crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of undesired vegetation in noncrop areas is also important. Many products are commercially available for these purposes, but the need continues for new compounds that are more effective, less costly, less toxic, environmentally safer or have different sites of action.

International patent application publication WO 2007/088876 discloses pyridone compounds of Formula i

wherein inter alia R₁ is C₁-C₆ alkyl; R₂ and R₃ are each independently hydrogen, cyano, or nitro; and A is a A-1 through A-5 as defined therein as herbicides.

The bis-nitrogen containing oxo and sulfono heterocycles of the present invention are not disclosed in this publication.

SUMMARY OF THE INVENTION

This invention is directed to compounds of Formula 1 (including all stereoisomers), N-oxides, and salts thereof, agricultural compositions containing them and their use as herbicides:

wherein

X is CH;

Y is C(O);

A is a radical selected from the group consisting of

B¹ and B³ are each independently a radical selected from the group consisting of

B² is a radical selected from the group consisting of

-   -   R¹ is phenyl, phenylsulfonyl, —W¹(phenyl), —W¹(S-phenyl),         —W¹(SO₂-phenyl), —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each         optionally substituted on ring members with up to five         substituents selected from R²¹; or -G or —W²G; or cyano,         hydroxy, amino, —C(═O)OH, —C(═O)NHCN, —C(═O)NHOH, —SO₂NH₂,         —SO₂NHCN, —SO₂NHOH, —NHCHO, C₁-C₁₀ alkyl, C₂-C₁₀ alkenyl, C₂-C₁₀         alkynyl, C₁-C₁₀ haloalkyl, C₂-C₁₀ haloalkenyl, C₂-C₁₂         haloalkynyl, C₃-C₁₂ cycloalkyl, C₃-C₁₂ halocycloalkyl, C₄-C₁₄         alkylcycloalkyl, C₄-C₁₄ cycloalkylalkyl, C₆-C₁₈         cycloalkylcycloalkyl, C₄-C₁₄ halocycloalkylalkyl, C₅-C₁₆         alkylcycloalkylalkyl, C₃-C₁₂ cycloalkenyl, C₃-C₁₂         halocycloalkenyl, C₂-C₁₂ alkoxyalkyl, C₃-C₁₂ alkoxyalkenyl,         C₄-C₁₄ alkylcycloalkyl, C₄-C₁₄ alkoxycycloalkyl, C₄-C₁₄         cycloalkoxyalkyl, C₅-C₁₄ cycloalkoxyalkoxyalkyl, C₃-C₁₄         alkoxyalkoxyalkyl, C₂-C₁₂ alkylthioalkyl, C₂-C₁₂         alkylsulfinylalkyl, C₂-C₁₂ alkylsulfonylalkyl, C₂-C₁₂         alkylaminoalkyl, C₃-C₁₄ dialkylaminoalkyl, C₂-C₁₂         haloalkylaminoalkyl, C₄-C₁₄ cycloalkylaminoalkyl, C₂-C₁₂         alkylcarbonyl, C₂-C₁₂ haloalkylcarbonyl, C₄-C₁₄         cycloalkylcarbonyl, C₂-C₁₂ alkoxycarbonyl, C₄-C₁₆         cycloalkoxycarbonyl, C₅-C₁₄ cycloalkylalkoxycarbonyl, C₂-C₁₂         alkylaminocarbonyl, C₃-C₁₄ dialkylaminocarbonyl, C₄-C₁₄         cycloalkylaminocarbonyl, C₂-C₉ cyanoalkyl, C₁-C₁₀ hydroxyalkyl,         C₄-C₁₄ cycloalkenylalkyl, C₂-C₁₂ haloalkoxyalkyl, C₂-C₁₂         alkoxyhaloalkyl, C₂-C₁₂ haloalkoxyhaloalkyl, C₄-C₁₄         halocycloalkoxyalkyl, C₄-C₁₄ cycloalkenyloxyalkyl, C₄-C₁₄         halocycloalkenyloxyalkyl, C₃-C₁₄ dialkoxyalkyl, C₃-C₁₄         alkoxyalkylcarbonyl, C₃-C₁₄ alkoxycarbonylalkyl, C₂-C₁₂         haloalkoxycarbonyl, C₁-C₁₀ alkoxy, C₁-C₁₀ haloalkoxy, C₃-C₁₂         cycloalkoxy, C₃-C₁₂ halocycloalkoxy, C₄-C₁₄ cycloalkylalkoxy,         C₂-C₁₀ alkenyloxy, C₂-C₁₀ haloalkenyloxy, C₂-C₁₀ alkynyloxy,         C₃-C₁₀ haloalkynyloxy, C₂-C₁₂ alkoxyalkoxy, C₂-C₁₂         alkylcarbonyloxy, C₂-C₁₂ haloalkylcarbonyloxy, C₄-C₁₄         cycloalkylcarbonyloxy, C₃-C₁₄ alkylcarbonylalkoxy, C₁-C₁₀         alkylthio, C₁-C₁₀ haloalkylthio, C₃-C₁₂ cycloalkylthio, C₁-C₁₀         alkylsulfinyl, C₁-C₁₀ haloalkylsulfinyl, C₁-C₁₀ alkylsulfonyl,         C₁-C₁₀ haloalkylsulfonyl, C₃-C₁₂ cycloalkylsulfonyl, C₂-C₁₂         alkylcarbonylthio, C₂-C₁₂ alkyl(thiocarbonyl)thio, C₃-C₁₂         cycloalkylsulfinyl, C₁-C₁₀ alkylaminosulfonyl, C₂-C₁₂         dialkylaminosulfonyl, C₁-C₁₀ alkylamino, C₂-C₁₂ dialkylamino,         C₁-C₁₀ haloalkylamino, C₂-C₁₂ halodialkylamino, C₃-C₁₂         cycloalkylamino, C₂-C₁₂ alkylcarbonylamino, C₂-C₁₂         haloalkylcarbonylamino, C₁-C₁₀ alkylsulfonylamino, C₁-C₁₀         haloalkylsulfonylamino or C₄-C₁₄ cycloalkyl(alkyl)amino;     -   W¹ is C₁-C₆ alkylene, C₂-C₆ alkenylene or C₂-C₆ alkynylene;     -   W² is C₁-C₆ alkylene;     -   R² is phenyl or —W³(phenyl), each optionally substituted on ring         members with up to five substituents selected from R²¹; or -G or         —W⁴G; or H, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH,         —C(═O)NH₂, —C(═S)NH₂, —C(═O)NHCN, —C(═O)NHOH, —SH, —SO₂NH₂,         —SO₂NHCN, —SO₂NHOH, —SF₅, —NHCHO, —NHNH₂, —NHOH, —NHCN,         —NHC(═O)NH₂, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆         haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈         cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀         cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl, C₄-C₁₀         halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈         cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₃-C₁₀         alkoxyalkenyl, C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀         alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈         alkylsulfinylalkyl, C₂-C₈ alkylsulfonylalkyl, C₂-C₈         alkylaminoalkyl, C₃-C₁₀ dialkylaminoalkyl, C₂-C₈         haloalkylaminoalkyl, C₄-C₁₀ cycloalkylaminoalkyl, C₂-C₈         alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀         cycloalkylcarbonyl, C₂-C₈ alkoxycarbonyl, C₄-C₁₀         cycloalkoxycarbonyl, C₅-C₁₂ cycloalkylalkoxycarbonyl, C₂-C₈         alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₄-C₁₀         cycloalkylaminocarbonyl, C₂-C₅ cyanoalkyl, C₁-C₆ hydroxyalkyl,         C₄-C₁₀ cycloalkenylalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈         alkoxyhaloalkyl, C₂-C₈ haloalkoxyhaloalkyl, C₄-C₁₀         halocycloalkoxyalkyl, C₄-C₁₀ cycloalkenyloxyalkyl, C₄-C₁₀         halocycloalkenyloxyalkyl, C₃-C₁₀ dialkoxyalkyl, C₃-C₁₀         alkoxyalkylcarbonyl, C₃-C₁₀ alkoxycarbonylalkyl, C₂-C₈         haloalkoxycarbonyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₈         cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀ cycloalkylalkoxy,         C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy, C₂-C₆ alkynyloxy, C₃-C₆         haloalkynyloxy, C₂-C₈ alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy,         C₂-C₈ haloalkylcarbonyloxy, C₄-C₁₀ cycloalkylcarbonyloxy, C₃-C₁₀         alkylcarbonylalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₃-C₈         cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl,         C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₃-C₈         cycloalkylsulfonyl, C₃-C₈ trialkylsilyl, C₃-C₈ cycloalkenyloxy,         C₃-C₈ halocycloalkenyloxy, C₂-C₈ haloalkoxyalkoxy, C₂-C₈         alkoxyhaloalkoxy, C₂-C₈ haloalkoxyhaloalkoxy, C₃-C₁₀         alkoxycarbonylalkoxy, C₂-C₈ alkyl(thiocarbonyl)oxy, C₂-C₈         alkylcarbonylthio, C₂-C₈ alkyl(thiocarbonyl)thio, C₃-C₈         cycloalkylsulfinyl, C₁-C₆ alkylaminosulfonyl, C₂-C₈         dialkylaminosulfonyl, C₃-C₁₀ halotrialkylsilyl, C₁-C₆         alkylamino, C₂-C₈ dialkylamino, C₁-C₆ haloalkylamino, C₂-C₈         halodialkylamino, C₃-C₈ cycloalkylamino, C₂-C₈         alkylcarbonylamino, C₂-C₈ haloalkylcarbonylamino, C₁-C₆         alkylsulfonylamino, C₁-C₆ haloalkylsulfonylamino or C₄-C₁₀         cycloalkyl(alkyl)amino; or     -   R¹ and R² are taken together along with the atoms to which they         are attached to make a 5-, 6- or 7-membered unsaturated,         partially unsaturated or fully unsaturated ring along with         members consisting of up to 2 oxygen atoms, 2 nitrogen atoms or         2 sulfur atoms or up to two —S(O)—, —S(O)₂—, —C(O)— groups         optionally substituted on carbon atom ring members selected from         halogen, cyano, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆         haloalkyl, C₃-C₈ cycloalkyl and C₂-C₈ alkoxyalkyl; and phenyl         optionally substituted with up to 5 substituents selected from         cyano, nitro, halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₁-C₆         haloalkoxy; and optionally substituted on nitrogen ring members         selected from H and C₁-C₆ alkyl; and phenyl optionally         substituted with up to 5 substituents selected from cyano,         nitro, halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₁-C₆ haloalkoxy;     -   W³ is C₁-C₆ alkylene, C₂-C₆ alkenylene or C₂-C₆ alkynylene;     -   W⁴ is C₁-C₆ alkylene;     -   R³ is H, halogen, cyano, hydroxy, —O⁻M⁺, amino, nitro, —CHO,         —C(═O)OH, —C(═O)NH₂, —C(═S)NH₂, —SH, —SO₂NH₂, —SO₂NHCN,         —SO₂NHOH, —OCN, —SCN, —SF₅, —NHNH₂, —NHOH, —N═C═O, —N═C═S, C₁-C₆         alkoxy, C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈         halocycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₂-C₆ alkenyloxy,         C₂-C₆ haloalkenyloxy, C₂-C₆ alkynyloxy, C₃-C₆ haloalkynyloxy,         C₂-C₈ alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy, C₂-C₈         haloalkylcarbonyloxy, C₄-C₁₀ cycloalkylcarbonyloxy, C₃-C₁₀         alkylcarbonylalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₃-C₈         cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl,         C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₃-C₈         cycloalkylsulfonyl, C₁-C₆ alkylsulfonyloxy, C₁-C₆ alkylamino,         C₂-C₈ dialkylamino, C₁-C₆ haloalkylamino, C₂-C₈         halodialkylamino, C₃-C₈ cycloalkylamino, C₂-C₈         alkylcarbonylamino, C₂-C₈ haloalkylcarbonylamino, C₁-C₆         alkylsulfonylamino or C₁-C₆ haloalkylsulfonylamino; or         benzyloxy, phenyloxy, benzylcarbonyloxy, phenylcarbonyloxy,         phenylsulfonyloxy, benzylsulfonyloxy, phenylthio, benzylthio,         phenylsulfinyl, benzylsulfinyl, phenylsulfonyl or         benzylsulfonyl, each optionally substituted on ring members with         up to five substituents selected from R²¹;     -   M⁺ is an alkali metal cation or an ammonium cation;     -   R⁴, R⁵, R⁶ and R⁷ are each independently H, halogen, hydroxy,         C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl,         C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy or C₃-C₈         halocycloalkoxy; or phenyl or benzyl, each optionally         substituted on ring members with up to five substituents         selected from R²¹;     -   R⁸ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆         haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈         cycloalkyl or C₃-C₈ halocycloalkyl; or benzyl optionally         substituted on ring members with up to five substituents         selected from R²¹;     -   R⁹ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆         haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈         cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀         cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl, C₄-C₁₀         halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈         cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀         cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl or C₂-C₈         alkylthioalkyl;     -   R¹⁰ is H, halogen, cyano, hydroxy, amino, nitro, SH, —SO₂NH₂,         —SO₂NHCN, —SO₂NHOH, —OCN, —SCN, —SF₅, —NHCHO, —NHNH₂, —N₃,         —NHOH, —NHCN, —NHC(═O)NH₂, —N═C═O, —N═C═S, C₁-C₆ alkyl, C₂-C₆         alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,         C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl,         C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄         cycloalkylcycloalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂         alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈         halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀ cycloalkoxyalkyl,         C₃-C₁₀ alkoxyalkoxyalkyl or C₂-C₈ alkylthioalkyl;     -   R¹¹ is H, halogen, cyano, hydroxy, amino, C₁-C₆ alkyl, C₂-C₆         alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,         C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl,         C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₄-C₁₀         halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈         cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀         cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈         alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl or C₂-C₈         alkylsulfonylalkyl; or phenyl optionally substituted with up to         five substituents selected from R²¹;     -   R¹² is H, halogen, cyano, hydroxy, amino, C₁-C₆ alkyl, C₂-C₆         alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,         C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl,         C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄         cycloalkylcycloalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂         alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl         or C₂-C₈ alkoxycarbonylamino;     -   R¹³ is H, halogen, cyano, hydroxy, amino, nitro or C₂-C₈         alkoxycarbonyl;     -   n is 0, 1, or 2;     -   each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is independently H, halogen, cyano,         hydroxy or C₁-C₆ alkyl; or     -   a pair of R¹⁴ and R¹⁸ is taken together as C₂-C₆ alkylene or         C₂-C₆ alkenylene;     -   R²⁰ is H, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₁-C₆ alkoxy,         C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy, C₁-C₆ alkyl, C₂-C₆ alkenyl,         C₂-C₆ alkynyl or C₃-C₈ cycloalkyl;     -   T is C₁-C₆ alkylene or C₂-C₆ alkenylene;     -   each G is independently a 5- or 6-membered heterocyclic ring or         an 8-, 9- or 10-membered fused bicyclic ring system, each ring         or ring system optionally substituted with up to five         substituents selected from R²¹ on carbon ring members and R²² on         nitrogen ring members;     -   each R²¹ is independently halogen, cyano, hydroxy, amino, nitro,         —CHO, —C(═O)OH, —C(═O)NH₂, —C(═S)NH₂, —C(═O)NHCN, —C(═O)NHOH,         —SH, —SO₂NH₂, —SO₂NHCN, —SO₂NHOH, —OCN, —SCN, —SF₅, C₁-C₆ alkyl,         C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆         haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈         halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl,         C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl,         C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈         alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈ alkoxyhaloalkyl,         C₂-C₅ cyanoalkyl, C₁-C₆ hydroxyalkyl, C₁-C₆ alkoxy, C₁-C₆         haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀         cycloalkylalkoxy, C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy, C₂-C₈         alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy, C₁-C₆ alkylthio, C₁-C₆         haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆         haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl,         C₃-C₈ cycloalkylsulfonyl, C₁-C₆ alkylamino, C₂-C₈ dialkylamino,         C₁-C₆ haloalkylamino, C₂-C₈ halodialkylamino or C₃-C₈         cycloalkylamino; and     -   each R²² is independently C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆         alkynyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl or C₂-C₈ alkoxyalkyl.

More particularly, this invention pertains to a compound of Formula 1 (including all stereoisomers), an N-oxide, or a salt thereof. This invention also relates to a herbicidal composition comprising a compound of the invention (i.e. in a herbicidally effective amount) and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents. This invention further relates to a method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of the invention (e.g., as a composition described herein)

This invention also relates to a herbicidal mixture of (a) a compound of Formula 1 and (b) at least one additional active ingredient.

This invention is also directed to an intermediate compound of Formula 1Q (including all stereoisomers), N-oxides, and salts thereof:

wherein A′ is a radical selected from the group consisting of

and R¹, R², B¹, B², B³, T, R⁹ and R¹⁰ are as defined above for a compound of Formula 1 which is useful for preparing a compound of Formula 1.

This invention is also directed to a compound of Formula 1R (including all stereoisomers), N-oxides, and salts thereof:

wherein

-   -   R¹ is phenyl, —W¹(phenyl), —W¹(S-phenyl), —W¹(SO₂-phenyl),         —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each optionally         substituted on ring members with up to five substituents         selected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl,         C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈         cycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl,         C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl,         C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈         alkylsulfinylalkyl or C₂-C₈ alkylsulfonylalkyl;     -   W¹ is C₁-C₆ alkylene, C₂-C₆ alkenylene or C₂-C₆ alkynylene;     -   W² is C₁-C₆ alkylene;     -   R² is phenyl or —W³(phenyl), each substituted on ring members         with up to two substituents selected from R²¹; or -G; or C₁-C₆         alkyl or C₃-C₈ cycloalkyl;     -   W³ is C₁-C₆ alkylene, C₂-C₆ alkenylene or C₂-C₆ alkynylene;     -   each G is independently a 5- or 6-membered heterocyclic ring or         an 8-, 9- or 10-membered fused bicyclic ring system, each ring         or ring system optionally substituted with up to five         substituents selected from R²¹ on carbon ring members and R²² on         nitrogen ring members;     -   each R²¹ is independently halogen, cyano, hydroxy, amino, nitro,         —CHO, —C(═O)OH, —C(═O)NH₂, —C(═S)NH₂, —C(═O)NHCN, —C(═O)NHOH,         —SH, —SO₂NH₂, —SO₂NHCN, —SO₂NHOH, —OCN, —SCN, —SF₅, C₁-C₆ alkyl,         C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆         haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈         halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl,         C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl,         C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈         alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈ alkoxyhaloalkyl,         C₂-C₅ cyanoalkyl, C₁-C₆ hydroxyalkyl, C₁-C₆ alkoxy, C₁-C₆         haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀         cycloalkylalkoxy, C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy, C₂-C₈         alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy, C₁-C₆ alkylthio, C₁-C₆         haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆         haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl,         C₃-C₈ cycloalkylsulfonyl, C₁-C₆ alkylamino, C₂-C₈ dialkylamino,         C₁-C₆ haloalkylamino, C₂-C₈ halodialkylamino or C₃-C₈         cycloalkylamino; and     -   each R²² is independently C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆         alkynyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl or C₂-C₈ alkoxyalkyl         which is useful for preparing a compound of Formula 1.

This invention is also directed to a compound of Formula 1S (including all stereoisomers), N-oxides, and salts thereof:

wherein

-   -   R¹ is phenyl, —W¹(phenyl), —W¹(S-phenyl), —W¹(SO₂-phenyl),         —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each optionally         substituted on ring members with up to five substituents         selected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl,         C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈         cycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl,         C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl,         C₃-C₁₀ alkoxyalkenyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀         alkoxycycloalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈         alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl or C₂-C₈         alkylsulfonylalkyl;     -   W¹ is C₁-C₆ alkylene, C₂-C₆ alkenylene or C₂-C₆ alkynylene;     -   W² is C₁-C₆ alkylene;     -   R² is phenyl or —W³(phenyl), each substituted on ring members         with up to two substituents selected from R²¹; or -G; or C₁-C₆         alkyl or C₃-C₈ cycloalkyl;     -   W³ is C₁-C₆ alkylene, C₂-C₆ alkenylene or C₂-C₆ alkynylene;     -   each G is independently a 5- or 6-membered heterocyclic ring or         an 8-, 9- or 10-membered fused bicyclic ring system, each ring         or ring system optionally substituted with up to five         substituents selected from R²¹ on carbon ring members and R²² on         nitrogen ring members;     -   each R²¹ is independently halogen, cyano, hydroxy, amino, nitro,         —CHO, —C(═O)OH, —C(═O)NH₂, —C(═S)NH₂, —C(═O)NHCN, —C(═O)NHOH,         —SH, —SO₂NH₂, —SO₂NHCN, —SO₂NHOH, —OCN, —SCN, —SF₅, C₁-C₆ alkyl,         C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆         haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈         halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl,         C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl,         C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈         alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈ alkoxyhaloalkyl,         C₂-C₅ cyanoalkyl, C₁-C₆ hydroxyalkyl, C₁-C₆ alkoxy, C₁-C₆         haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀         cycloalkylalkoxy, C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy, C₂-C₈         alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy, C₁-C₆ alkylthio, C₁-C₆         haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆         haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl,         C₃-C₈ cycloalkylsulfonyl, C₁-C₆ alkylamino, C₂-C₈ dialkylamino,         C₁-C₆ haloalkylamino, C₂-C₈ halodialkylamino or C₃-C₈         cycloalkylamino;     -   each R²² is independently C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆         alkynyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl or C₂-C₈ alkoxyalkyl;         and     -   R²³ is an optionally substituted carbon moiety         which is useful for preparing a compound of Formula 1.

This invention is also directed to a process for preparing a compound of Formula 1 from a compound of formula 1Q in the presence of cesium fluoride:

wherein A′ is a radical selected from A′-1, A′-2, A′-3 and A′-5 as defined above for a compound of Formula 1Q; and A is radical selected from A-1, A-2, A-3 and A-5 as defined above for a compound of Formula 1; and R¹ and R² are as defined above for a compound of Formula 1 which is useful for preparing a compound of Formula 1.

This invention is also directed to compounds of Formula 1P (including all stereoisomers), N-oxides, and salts thereof, agricultural compositions containing them and their use as herbicides:

wherein

X is CH or N;

Y is C(O) or S(O)₂; provided that when Y is S(O)₂, then X is CH;

A is a radical selected from the group consisting of

B¹ and B³ are each independently a radical selected from the group consisting of

B² is a radical selected from the group consisting of

-   -   R¹ is phenyl, phenylsulfonyl, —W¹(phenyl), —W¹(S-phenyl),         —W¹(SO₂-phenyl), —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each         optionally substituted on ring members with up to five         substituents selected from R²¹; or -G or —W²G; or cyano,         hydroxy, amino, —C(═O)OH, —C(═O)NHCN, —C(═O)NHOH, —SO₂NH₂,         —SO₂NHCN, —SO₂NHOH, —NHCHO, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆         alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl,         C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀ alkylcycloalkyl,         C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl, C₄-C₁₀         halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈         cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀         cycloalkoxyalkyl, C₅-C₁₀ cycloalkoxyalkoxyalkyl, C₃-C₁₀         alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈         alkylsulfinylalkyl, C₂-C₈ alkylsulfonylalkyl, C₂-C₈         alkylaminoalkyl, C₃-C₁₀ dialkylaminoalkyl, C₂-C₈         haloalkylaminoalkyl, C₄-C₁₀ cycloalkylaminoalkyl, C₂-C₈         alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀         cycloalkylcarbonyl, C₂-C₈ alkoxycarbonyl, C₄-C₁₀         cycloalkoxycarbonyl, C₅-C₁₂ cycloalkylalkoxycarbonyl, C₂-C₈         alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₄-C₁₀         cycloalkylaminocarbonyl, C₂-C₅ cyanoalkyl, C₁-C₆ hydroxyalkyl,         C₄-C₁₀ cycloalkenylalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈         alkoxyhaloalkyl, C₂-C₈ haloalkoxyhaloalkyl, C₄-C₁₀         halocycloalkoxyalkyl, C₄-C₁₀ cycloalkenyloxyalkyl, C₄-C₁₀         halocycloalkenyloxyalkyl, C₃-C₁₀ dialkoxyalkyl, C₃-C₁₀         alkoxyalkylcarbonyl, C₃-C₁₀ alkoxycarbonylalkyl, C₂-C₈         haloalkoxycarbonyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₈         cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀ cycloalkylalkoxy,         C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy, C₂-C₆ alkynyloxy, C₃-C₆         haloalkynyloxy, C₂-C₈ alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy,         C₂-C₈ haloalkylcarbonyloxy, C₄-C₁₀ cycloalkylcarbonyloxy, C₃-C₁₀         alkylcarbonylalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₃-C₈         cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl,         C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₃-C₈         cycloalkylsulfonyl, C₂-C₈ alkylcarbonylthio, C₂-C₈         alkyl(thiocarbonyl)thio, C₃-C₈ cycloalkylsulfinyl, C₁-C₆         alkylaminosulfonyl, C₂-C₈ dialkylaminosulfonyl, C₁-C₆         alkylamino, C₂-C₈ dialkylamino, C₁-C₆ haloalkylamino, C₂-C₈         halodialkylamino, C₃-C₈ cycloalkylamino, C₂-C₈         alkylcarbonylamino, C₂-C₈ haloalkylcarbonylamino, C₁-C₆         alkylsulfonylamino, C₁-C₆ haloalkylsulfonylamino or C₄-C₁₀         cycloalkyl(alkyl)amino;     -   W¹ is C₁-C₆ alkylene, C₂-C₆ alkenylene or C₂-C₆ alkynylene;     -   W² is C₁-C₆ alkylene;     -   R² is phenyl or —W³(phenyl), each optionally substituted on ring         members with up to five substituents selected from R²¹; or -G or         —W⁴G; or H, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH,         —C(═O)NH₂, —C(═S)NH₂, —C(═O)NHCN, —C(═O)NHOH, —SH, —SO₂NH₂,         —SO₂NHCN, —SO₂NHOH, —SF₅, —NHCHO, —NHNH₂, —NHOH, —NHCN,         —NHC(═O)NH₂, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆         haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈         cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀         cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl, C₄-C₁₀         halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈         cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀         cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈         alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈         alkylsulfonylalkyl, C₂-C₈ alkylaminoalkyl, C₃-C₁₀         dialkylaminoalkyl, C₂-C₈ haloalkylaminoalkyl, C₄-C₁₀         cycloalkylaminoalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈         haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈         alkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₅-C₁₂         cycloalkylalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀         dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₂-C₅         cyanoalkyl, C₁-C₆ hydroxyalkyl, C₄-C₁₀ cycloalkenylalkyl, C₂-C₈         haloalkoxyalkyl, C₂-C₈ alkoxyhaloalkyl, C₂-C₈         haloalkoxyhaloalkyl, C₄-C₁₀ halocycloalkoxyalkyl, C₄-C₁₀         cycloalkenyloxyalkyl, C₄-C₁₀ halocycloalkenyloxyalkyl, C₃-C₁₀         dialkoxyalkyl, C₃-C₁₀ alkoxyalkylcarbonyl, C₃-C₁₀         alkoxycarbonylalkyl, C₂-C₈ haloalkoxycarbonyl, C₁-C₆ alkoxy,         C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy,         C₄-C₁₀ cycloalkylalkoxy, C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy,         C₂-C₆ alkynyloxy, C₃-C₆ haloalkynyloxy, C₂-C₈ alkoxyalkoxy,         C₂-C₈ alkylcarbonyloxy, C₂-C₈ haloalkylcarbonyloxy, C₄-C₁₀         cycloalkylcarbonyloxy, C₃-C₁₀ alkylcarbonylalkoxy, C₁-C₆         alkylthio, C₁-C₆ haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆         alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl,         C₁-C₆ haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₃-C₈         trialkylsilyl, C₃-C₈ cycloalkenyloxy, C₃-C₈ halocycloalkenyloxy,         C₂-C₈ haloalkoxyalkoxy, C₂-C₈ alkoxyhaloalkoxy, C₂-C₈         haloalkoxyhaloalkoxy, C₃-C₁₀ alkoxycarbonylalkoxy, C₂-C₈         alkyl(thiocarbonyl)oxy, C₂-C₈ alkylcarbonylthio, C₂-C₈         alkyl(thiocarbonyl)thio, C₃-C₈ cycloalkylsulfinyl, C₁-C₆         alkylaminosulfonyl, C₂-C₈ dialkylaminosulfonyl, C₃-C₁₀         halotrialkylsilyl, C₁-C₆ alkylamino, C₂-C₈ dialkylamino, C₁-C₆         haloalkylamino, C₂-C₈ halodialkylamino, C₃-C₈ cycloalkylamino,         C₂-C₈ alkylcarbonylamino, C₂-C₈ haloalkylcarbonylamino, C₁-C₆         alkylsulfonylamino, C₁-C₆ haloalkylsulfonylamino or C₄-C₁₀         cycloalkyl(alkyl)amino;     -   W³ is C₁-C₆ alkylene, C₂-C₆ alkenylene or C₂-C₆ alkynylene;     -   W⁴ is C₁-C₆ alkylene;     -   R³ is H, halogen, cyano, hydroxy, —O⁻M⁺, amino, nitro, —CHO,         —C(═O)OH, —C(═O)NH₂, —C(═S)NH₂, —SH, —SO₂NH₂, —SO₂NHCN,         —SO₂NHOH, —OCN, —SCN, —SF₅, —NHNH₂, —NHOH, —N═C═O, —N═C═S, C₁-C₆         alkoxy, C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈         halocycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₂-C₆ alkenyloxy,         C₂-C₆ haloalkenyloxy, C₂-C₆ alkynyloxy, C₃-C₆ haloalkynyloxy,         C₂-C₈ alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy, C₂-C₈         haloalkylcarbonyloxy, C₄-C₁₀ cycloalkylcarbonyloxy, C₃-C₁₀         alkylcarbonylalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₃-C₈         cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl,         C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₃-C₈         cycloalkylsulfonyl, C₁-C₆ alkylsulfonyloxy, C₁-C₆ alkylamino,         C₂-C₈ dialkylamino, C₁-C₆ haloalkylamino, C₂-C₈         halodialkylamino, C₃-C₈ cycloalkylamino, C₂-C₈         alkylcarbonylamino, C₂-C₈ haloalkylcarbonylamino, C₁-C₆         alkylsulfonylamino or C₁-C₆ haloalkylsulfonylamino; or         benzyloxy, phenyloxy, benzylcarbonyloxy, phenylcarbonyloxy,         phenylsulfonyloxy, benzylsulfonyloxy, phenylthio, benzylthio,         phenylsulfinyl, benzylsulfinyl, phenylsulfonyl or         benzylsulfonyl, each optionally substituted on ring members with         up to five substituents selected from R²¹;     -   M⁺ is an alkali metal cation or an ammonium cation;     -   R⁴, R⁵, R⁶ and R⁷ are each independently H, halogen, hydroxy,         C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl,         C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy or C₃-C₈         halocycloalkoxy; or phenyl or benzyl, each optionally         substituted on ring members with up to five substituents         selected from R²¹;     -   R⁸ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆         haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈         cycloalkyl or C₃-C₈ halocycloalkyl; or benzyl optionally         substituted on ring members with up to five substituents         selected from R²¹;     -   R⁹ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆         haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈         cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀         cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl, C₄-C₁₀         halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈         cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀         cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl or C₂-C₈         alkylthioalkyl;     -   R¹⁰ is H, halogen, cyano, hydroxy, amino, nitro, SH, —SO₂NH₂,         —SO₂NHCN, —SO₂NHOH, —OCN, —SCN, —SF₅, —NHCHO, —NHNH₂, —N₃,         —NHOH, —NHCN, —NHC(═O)NH₂, —N═C═O, —N═C═S, C₁-C₆ alkyl, C₂-C₆         alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,         C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl,         C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄         cycloalkylcycloalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂         alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈         halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀ cycloalkoxyalkyl,         C₃-C₁₀ alkoxyalkoxyalkyl or C₂-C₈ alkylthioalkyl;     -   R¹¹ is H, halogen, cyano, hydroxy, amino, C₁-C₆ alkyl, C₂-C₆         alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,         C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl,         C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₄-C₁₀         halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈         cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀         cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈         alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl or C₂-C₈         alkylsulfonylalkyl; or phenyl optionally substituted with up to         five substituents selected from R²¹;     -   R¹² is H, halogen, cyano, hydroxy, amino, C₁-C₆ alkyl, C₂-C₆         alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,         C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl,         C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄         cycloalkylcycloalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂         alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl         or C₂-C₈ alkoxycarbonylamino;     -   R¹³ is H, halogen, cyano, hydroxy, amino, nitro or C₂-C₈         alkoxycarbonyl;     -   n is 0, 1, or 2;     -   each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is independently H, halogen, cyano,         hydroxy or C₁-C₆ alkyl; or     -   a pair of R¹⁴ and R¹⁸ is taken together as C₂-C₆ alkylene or         C₂-C₆ alkenylene;     -   R²⁰ is H, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₁-C₆ alkoxy,         C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy, C₁-C₆ alkyl, C₂-C₆ alkenyl,         C₂-C₆ alkynyl or C₃-C₈ cycloalkyl;     -   T is C₁-C₆ alkylene or C₂-C₆ alkenylene;     -   each G is independently a 5- or 6-membered heterocyclic ring or         an 8-, 9- or 10-membered fused bicyclic ring system, each ring         or ring system optionally substituted with up to five         substituents selected from R²¹ on carbon ring members and R²² on         nitrogen ring members;     -   each R²¹ is independently halogen, cyano, hydroxy, amino, nitro,         —CHO, —C(═O)OH, —C(═O)NH₂, —C(═S)NH₂, —C(═O)NHCN, —C(═O)NHOH,         —SH, —SO₂NH₂, —SO₂NHCN, —SO₂NHOH, —OCN, —SCN, —SF₅, C₁-C₆ alkyl,         C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆         haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈         halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl,         C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl,         C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈         alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈ alkoxyhaloalkyl,         C₂-C₅ cyanoalkyl, C₁-C₆ hydroxyalkyl, C₁-C₆ alkoxy, C₁-C₆         haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀         cycloalkylalkoxy, C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy, C₂-C₈         alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy, C₁-C₆ alkylthio, C₁-C₆         haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆         haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl,         C₃-C₈ cycloalkylsulfonyl, C₁-C₆ alkylamino, C₂-C₈ dialkylamino,         C₁-C₆ haloalkylamino, C₂-C₈ halodialkylamino or C₃-C₈         cycloalkylamino; and     -   each R²² is independently C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆         alkynyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl or C₂-C₈ alkoxyalkyl.

More particularly, this invention pertains to a compound of Formula 1P (including all stereoisomers), an N-oxide, or a salt thereof. This invention also relates to a herbicidal composition comprising a compound of the invention (i.e. in a herbicidally effective amount) and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents. This invention further relates to a method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of the invention (e.g., as a composition described herein).

This invention also includes a herbicidal mixture of (a) a compound of Formula 1P and (b) an active ingredient selected from a photosystem II inhibitor.

DETAILS OF THE INVENTION

As used herein, the terms “comprises,” “comprising,” “includes,” “including,” “has,” “having,” “contains”, “containing,” “characterized by” or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitation explicitly indicated. For example, a composition, mixture, process or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process or method.

The transitional phrase “consisting of” excludes any element, step, or ingredient not specified. If in the claim, such would close the claim to the inclusion of materials other than those recited except for impurities ordinarily associated therewith. When the phrase “consisting of” appears in a clause of the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause; other elements are not excluded from the claim as a whole.

The transitional phrase “consisting essentially of” is used to define a composition or method that includes materials, steps, features, components, or elements, in addition to those literally disclosed, provided that these additional materials, steps, features, components, or elements do not materially affect the basic and novel characteristic(s) of the claimed invention. The term “consisting essentially of” occupies a middle ground between “comprising” and “consisting of”.

Where applicants have defined an invention or a portion thereof with an open-ended term such as “comprising,” it should be readily understood that (unless otherwise stated) the description should be interpreted to also describe such an invention using the terms “consisting essentially of” or “consisting of.”

Further, unless expressly stated to the contrary, “or” refers to an inclusive “or” and not to an exclusive “or”. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).

Also, the indefinite articles “a” and “an” preceding an element or component of the invention are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or component. Therefore “a” or “an” should be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously meant to be singular.

As referred to herein, the term “seedling”, used either alone or in a combination of words means a young plant developing from the embryo of a seed.

As referred to herein, the term “broadleaf” used either alone or in words such as “broadleaf weed” means dicot or dicotyledon, a term used to describe a group of angiosperms characterized by embryos having two cotyledons.

As used herein, the term “alkylating agent” refers to a chemical compound in which a carbon-containing radical is bound through a carbon atom to a leaving group such as halide or sulfonate, which is displaceable by bonding of a nucleophile to said carbon atom. Unless otherwise indicated, the term “alkylating” does not limit the carbon-containing radical to alkyl; the carbon-containing radicals in alkylating agents include the variety of carbon-bound substituent radicals specified for R¹, R² and R³.

In the above recitations, the term “alkyl”, used either alone or in compound words such as “alkylthio” or “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, i-propyl, or the different butyl, pentyl or hexyl isomers. “Alkenyl” includes straight-chain or branched alkenes such as ethenyl, 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. “Alkenyl” also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. “Alkynyl” includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. “Alkynyl” can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl. “Alkylene” denotes a straight-chain or branched alkanediyl. Examples of “alkylene” include CH₂, CH₂CH₂, CH(CH₃), CH₂CH₂CH₂, CH₂CH(CH₃) and the different butylene isomers. “Alkenylene” denotes a straight-chain or branched alkenediyl containing one olefinic bond. Examples of “alkenylene” include CH═CH, CH₂CH═CH, CH═C(CH₃) and the different butenylene isomers. “Alkynylene” denotes a straight-chain or branched alkynediyl containing one triple bond. Examples of “alkynylene” include C≡C, CH₂C≡C, C≡CCH₂ and the different butynylene isomers.

“Alkoxy” includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. “Alkoxyalkyl” denotes alkoxy substitution on alkyl. Examples of “alkoxyalkyl” include CH₃OCH₂, CH₃OCH₂CH₂, CH₃CH₂OCH₂, CH₃CH₂CH₂CH₂OCH₂ and CH₃CH₂OCH₂CH₂. “Alkoxyalkoxy” denotes alkoxy substitution on alkoxy. “Alkenyloxy” includes straight-chain or branched alkenyloxy moieties. Examples of “alkenyloxy” include H₂C═CHCH₂O, (CH₃)₂C═CHCH₂O, (CH₃)CH═CHCH₂O, (CH₃)CH═C(CH₃)CH₂O and CH₂═CHCH₂CH₂O. “Alkynyloxy” includes straight-chain or branched alkynyloxy moieties. Examples of “alkynyloxy” include HC≡CCH₂O, CH₃C≡CCH₂O and CH₃C≡CCH₂CH₂O. “Alkoxyalkenyl” includes straight-chain or branched alkenyl substituted by an alkoxy group. Examples of “alkoxyalkenyl” include CH₃OCH═CH, CH₃C(OCH₃)═CH and CH₃CH₂OCH═CHCH₂. “Alkoxyalkoxyalkyl” denotes alkoxyalkoxy substitution on alkyl. Examples of “alkoxyalkoxyalkyl” include CH₃OCH₂OCH₂, CH₃OCH₂OCH₂CH₂, CH₃CH₂OCH₂OCH₂ and CH₃OCH₃CH₂OCH₂CH₂. “Alkylthio” includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers. “Alkylsulfinyl” includes both enantiomers of an alkylsulfinyl group. Examples of “alkylsulfinyl” include CH₃S(O)—, CH₃CH₂S(O)—, CH₃CH₂CH₂S(O)—, (CH₃)₂CHS(O)— and the different butylsulfonyl, pentylsulfinyl and hexylsulfinyl isomers. Examples of “alkylsulfonyl” include CH₃S(O)₂—, CH₃CH₂S(O)₂—, CH₃CH₂CH₂S(O)₂—, (CH₃)₂CHS(O)₂—, and the different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers. The terms “cycloalkylsulfinyl” and “cycloalkylsulfonyl are defined analogously to the terms “alkylsulfinyl” and “alkylsulfonyl” above.

“Alkylthioalkyl” denotes alkylthio substitution on alkyl. Examples of “alkylthioalkyl” include CH₃SCH₂, CH₃SCH₂CH₂, CH₃CH₂SCH₂, CH₃CH₂CH₂CH₂SCH₂ and CH₃CH₂SCH₂CH₂; “alkylsulfinylalkyl” and “alkylsulfonylalkyl” include the corresponding sulfoxides and sulfones, respectively. “Alkylamino” includes an NH radical substituted with straight-chain or branched alkyl. Examples of “alkylamino” include CH₃CH₂NH, CH₃CH₂CH₂NH, and (CH₃)₂CHCH₂NH. Examples of “dialkylamino” include (CH₃)₂N, (CH₃CH₂CH₂)₂N and CH₃CH₂(CH₃)N. “Alkylaminoalkyl” denotes alkylamino substitution on alkyl. Examples of “alkylaminoalkyl” include CH₃NHCH₂, CH₃NHCH₂CH₂, CH₃CH₂NHCH₂, CH₃CH₂CH₂CH₂NHCH₂ and CH₃CH₂NHCH₂CH₂. Examples of “dialkylaminoalkyl” include ((CH₃)₂CH)₂NCH₂, (CH₃CH₂CH₂)₂NCH₂ and CH₃CH₂(CH₃)NCH₂CH₂. The term “alkylcarbonylamino” denotes alkyl bonded to a C(═O)NH moiety. Examples of “alkylcarbonylamino” include CH₃CH₂C(═O)NH and CH₃ CH₂CH₂C(═O)NH.

“Alkylcarbonylthio” denotes a straight-chain or branched alkylcarbonyl attached to and linked through a sulfur atom. Examples of “alkylcarbonylthio” include CH₃C(═O)S, CH₃CH₂CH₂C(═O)S and (CH₃)₂CHC(═O)S. The term “alkyl(thiocarbonyl)oxy” refers to an alkylsulfinyl moiety group bonded to an oxygen atom. Examples of “alkyl(thiocarbonyl)oxy”, include CH₃CH₂OS(O) and CH₃CH₂CH₂OS(O). The term “alkyl(thiocarbonyl)thio” refers to an alkylsulfinyl moiety bonded to a sulfur atom. Examples “alkyl(thiocarbonyl)thio” include CH₃CH₂S(O)S.

“Trialkylsilyl” includes 3 branched and/or straight-chain alkyl radicals attached to and linked through a silicon atom, such as trimethylsilyl, triethylsilyl and tert-butyldimethylsilyl. Examples of “halotrialkylsilyl” include CF₃(CH₃)₂Si—, (CF₃)₃Si—, and CH₂Cl(CH₃)₂Si—. “Hydroxyalkyl” denotes an alkyl group substituted with one hydroxy group. Examples of “hydroxyalkyl” include HOCH₂CH₂, CH₃CH₂(OH)CH and HOCH₂CH₂CH₂CH₂. “Cyanoalkyl” denotes an alkyl group substituted with one cyano group. Examples of “cyanoalkyl” include NCCH₂, NCCH₂CH₂ and CH₃CH(CN)CH₂.

“Cycloalkyl” includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. The term “alkylcycloalkyl” denotes alkyl substitution on a cycloalkyl moiety and includes, for example, ethylcyclopropyl, i-propylcyclobutyl, 3-methylcyclopentyl and 4-methylcyclohexyl. The term “cycloalkylalkyl” denotes cycloalkyl substitution on an alkyl moiety. Examples of “cycloalkylalkyl” include cyclopropylmethyl, cyclopentylethyl, and other cycloalkyl moieties bonded to straight-chain or branched alkyl groups. The term “cycloalkoxy” denotes cycloalkyl linked through an oxygen atom such as cyclopentyloxy and cyclohexyloxy. The term “alkylcycloalkyl” denotes alkyl substitution on a cycloalkyl moiety. Examples of “alkylcycloalkyl” include methylcyclopropyl, ethylcyclopentyl, and other straight-chain or branched alkyl groups bonded to cycloalkyl moiety. The term “alkoxycycloalkyl” denotes alkoxy substitution on a cycloalkyl moiety. Examples of “alkoxycycloalkyl” include methoxycyclopropyl, ethoxycyclopentyl, and other straight-chain or branched alkoxy groups bonded to a cycloalkyl moiety. “Cycloalkylalkoxy” denotes cycloalkylalkyl linked through an oxygen atom attached to the alkyl chain. Examples of “cycloalkylalkoxy” include cyclopropylmethoxy, cyclopentylethoxy, and other cycloalkyl moieties bonded to straight-chain or branched alkoxy groups. Examples of “cyanocycloalkyl” include 4-cyanocyclohexyl and 3-cyanocyclopentyl. “Cycloalkenyl” includes groups such as cyclopentenyl and cyclohexenyl as well as groups with more than one double bond such as 1,3- and 1,4-cyclohexadienyl.

The term “halogen”, either alone or in compound words such as “haloalkyl”, or when used in descriptions such as “alkyl substituted with halogen” includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl”, or when used in descriptions such as “alkyl substituted with halogen” said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” or “alkyl substituted with halogen” include F₃C—, ClCH₂—, CF₃CH₂— and CF₃CCl₂—. The terms “halocycloalkyl”, “haloalkoxy”, “haloalkylthio”, haloalkylsulfinyl, haloalkylsulfonyl, “haloalkenyloxy”, “haloalkynyloxy” “haloalkenyl”, “haloalkynyl”, “haloalkoxyalkyl”, “haloalkoxyalkoxy” “haloalkoxyhaloalkoxy”, “haloalkoxyhaloalkyl”, “halo alkylamino”, “haloalkylaminoalkyl” “halocycloalkoxy”, “halocycloalkoxyalkyl”, “halocycloalkylalkyl”, “halocycloalkenyl”, “halocycloalkenyloxy”, “halocycloalkenyloxy”, “halocycloalkenyloxyalkyl”, “alkoxyhaloalkoxy”, alkoxyhaloalkyl, haloalkylcarbonyloxy, and the like, are defined analogously to the term “haloalkyl”. Examples of “haloalkoxy” include CF₃O—, CCl₃CH₂O—, HCF₂CH₂CH₂O— and CF₃CH₂O—. Examples of “haloalkylthio” include CCl₃S—, CF₃S—, CCl₃CH₂S— and ClCH₂CH₂CH₂S—. Examples of “haloalkylsulfinyl” include CF₃S(O)—, CCl₃S(O)—, CF₃CH₂S(O)— and CF₃CF₂S(O)—. Examples of “haloalkylsulfonyl” include CF₃S(O)₂—, CCl₃S(O)₂—, CF₃CH₂S(O)₂— and CF₃CF₂S(O)₂—. Examples of “haloalkenyl” include (Cl)₂C═CHCH₂— and CF₃CH₂CH═CHCH₂—. Examples of “haloalkynyl” include HC≡CCHCl—, CF₃C≡C—, CCl₃C≡C— and FCH₂C≡CCH₂—. Examples of “haloalkoxyalkoxy” include CF₃OCH₂O—, ClCH₂CH₂OCH₂CH₂O—, Cl₃CCH₂OCH₂O— as well as branched alkyl derivatives. Examples of “haloalkylamino” include CF₃(CH₃)CHNH, (CF₃)₂CHNH and CH₂ClCH₂NH. The term “halodialkyl”, either alone or in compound words such as “halodialkylamino”, means at least one of the two alkyl groups is substituted with at least one halogen atom, and independently each halogenated alkyl group may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “halodialkylamino” include (BrCH₂CH₂)₂N and BrCH₂CH₂(ClCH₂CH₂)N.

“Alkylcarbonyl” denotes a straight-chain or branched alkyl moieties bonded to a C(═O) moiety. Examples of “alkylcarbonyl” include CH₃C(═O)—, CH₃CH₂CH₂C(═O)— and (CH₃)₂CHC(═O)—. Examples of “alkoxycarbonyl” include CH₃OC(═O)—, CH₃CH₂OC(═O)—, CH₃CH₂CH₂OC(═O)—, (CH₃)₂CHOC(═O)— and the different butoxy- or pentoxycarbonyl isomers. The terms “haloalkylcarbonyl” “haloalkoxycarbonyl”, “alkoxyalkylcarbonyl”, “cycloalkoxycarbonyl”, “cycloalkylalkoxycarbonyl”, “cycloalkylaminocarbonyl” are defined analogously.

The term “alkoxycarbonylamino” denotes a straight-chain or branched alkoxy moieties bonded to a C(═O) moiety of carbonylamino group. Examples of “alkoxycarbonylamino” include CH₃OC(═O)NH— and CH₃CH₂OC(═O)NH—. Examples of “alkylaminocarbonyl” include CH₃NHC(═O), CH₃CH₂NHC(═O), CH₃CH₂CH₂NHC(═O), (CH₃)₂CHNHC(═O) and the different butylamino- or pentylaminocarbonyl isomers. Examples of “dialkylaminocarbonyl” include (CH₃)₂NC(═O), (CH₃CH₂)₂NC(═O), CH₃CH₂(CH₃)NC(═O), (CH₃)₂CH(CH₃)NC(═O) and CH₃CH₂CH₂(CH₃)NC(═O). The term “alkylcarbonyloxy” denotes straight-chain or branched alkyl bonded to a C(═O)O moiety. Examples of “alkylcarbonyloxy” include CH₃CH₂C(═O)O and (CH₃)₂CHC(═O)O. The term “alkylcarbonylalkoxy” denotes alkylcarbonyl bonded to an alkoxy moiety. Examples of “alkylcarbonylalkoxy” include CH₃C(═O)CH₂CH₂O and CH₃CH₂C(═O)CH₂O. Examples of “alkoxycarbonyloxy” include CH₃CH₂CH₂OC(═O)O and (CH₃)₂CHOC(═O)O. The term “cycloalkylcarbonyloxy” denotes a cycloalkylcarbonyl group bonded to oxygen. Examples of “cycloalkylcarbonyloxy” include c-Pr—C(O)O— and c-hexyl-C(O)O—.

“Alkylsulfonylamino” denotes an NH radical substituted with alkylsulfonyl. Examples of “alkylsulfonylamino” include CH₃CH₂S(═O)₂NH— and (CH₃)₂CHS(═O)₂NH—. The term “alkylsulfonyloxy” denotes an alkylsulfonyl group bonded to an oxygen atom. Examples of “alkylsulfonyloxy” include CH₃S(═O)₂O —, CH₃CH₂S(═O)₂O—, CH₃CH₂CH₂S(═O)₂O—, (CH₃)₂CHS(═O)₂O—, and the different butylsulfonyloxy, pentylsulfonyloxy and hexylsulfonyloxy isomers.

The term “cycloalkoxyalkyl” denotes cycloalkoxy substitution on an alkyl moiety. Examples of “cycloalkoxyalkyl” include cyclopropyloxymethyl, cyclopentyloxyethyl, and other cycloalkoxy moieties bonded to straight-chain or branched alkyl groups. The term “cycloalkylthio” denotes cycloalkyl attached to and linked through a sulfur atom such as cyclopropylthio and cyclopentylthio; “cycloalkylsulfonyl” includes the corresponding sulfones. “Alkylcycloalkylalkyl” denotes an alkyl group substituted with alkylcycloalkyl. Examples of “alkylcycloalkylalkyl” include 1-, 2-, 3- or 4-methyl or -ethyl cyclohexylmethyl. The term “cycloalkoxyalkoxyalkyl” denotes a cycloalkoxy moiety attached to an alkoxyalkyl group. Examples of the term “cycloalkoxyalkoxyalkyl” include (tetrahydrofuran-2-yl)CH₂OCH₂—, (tetrahydrofuran-3-yl)CH₂CH₂O CH₂— or (oxiran-2-yl)CH₂OCH₂CH₂—. The term “cycloalkylcycloalkyl” denotes cycloalkyl substitution on another cycloalkyl ring, wherein each cycloalkyl ring independently has from 3 to 7 carbon atom ring members. Examples of cycloalkylcycloalkyl include cyclopropylcyclopropyl (such as 1,1′-bicyclopropyl-1-yl, 1,1′-bicyclopropyl-2-yl), cyclohexylcyclopentyl (such as 4-cyclopentylcyclohexyl) and cyclohexylcyclohexyl (such as 1,1′-bicyclohexyl-1-yl), and the different cis- and trans-cycloalkylcycloalkyl isomers, (such as (1R,2S)-1,1′-bicyclopropyl-2-yl and (1R,2R)-1,1′-bicyclopropyl-2-yl).

“Dialkoxyalkyl” denotes two independent alkoxy groups substituted on same carbon of the alkyl group. Examples of “dialkoxyalkyl” include (CH₃O)₂CH— and CH₃CH₂O(CH₃O)CH—. “Cycloalkylamino” denotes an NH radical substituted with cycloalkyl. Examples of “cycloalkylamino” include cyclopropylamino and cyclohexylamino. “Cycloalkyl(alkyl)amino” means a cycloalkylamino group where the hydrogen atom is replaced by an alkyl radical. Examples of “cycloalkyl(alkyl)amino” include groups such as cyclopropyl(methyl)amino, cyclobutyl(butyl)amino, cyclopentyl(propyl)amino, cyclohexyl(methyl)amino and the like. The term “cycloalkylaminoalkyl” denotes cycloalkylamino substitution on an alkyl group. Examples of “cycloalkylaminoalkyl” include cyclopropylaminomethyl, cyclopentylaminoethyl, and other cycloalkylamino moieties bonded to straight-chain or branched alkyl groups.

“Cycloalkylcarbonyl” denotes cycloalkyl bonded to a C(═O) group including, for example, cyclopropylcarbonyl and cyclopentylcarbonyl. The term “cycloalkoxycarbonyl” means cycloalkoxy bonded to a C(═O) group, for example, cyclopropyloxycarbonyl and cyclopentyloxycarbonyl. “Cycloalkylaminocarbonyl” denotes cycloalkylamino bonded to a C(═O) group, for example, cyclopentylaminocarbonyl and cyclohexylaminocarbonyl. “Cycloalkylalkoxycarbonyl” denotes cycloalkylalkoxy bonded to a C(═O) group. Examples of “cycloalkylalkoxycarbonyl” include cyclopropylethoxycarbonyl and cyclopentylmethoxycarbonyl. “Cycloalkylcarbonyloxy” denotes cycloalkylcarbonyl attached to and linked through an oxygen atom. Examples of “cycloalkylcarbonyloxy” include cyclohexylcarbonyloxy and cyclopentylcarbonyloxy.

The term “cycloalkenylalkyl” denotes cycloalkenyl substitution on an alkyl moiety. Examples of “cycloalkenylalkyl” include cyclobutenylmethyl, cyclopentenylethyl, and other cycloalkenyl moieties bonded to straight-chain or branched alkyl groups. The term “cycloalkenyloxy” denotes cycloalkenyl linked through an oxygen atom such as cyclopentenyloxy and cyclohexenyloxy. The term “cycloalkenyloxyalkyl” denotes cycloalkenyloxy substitution on an alkyl moiety. Examples of “cycloalkenyloxyalkyl” include cyclobutenyloxymethyl, cyclopentenyloxyethyl, and other cycloalkenyloxy moieties bonded to straight-chain or branched alkyl groups.

The term “alkylaminosulfonyl” denotes a straight-chain or branched alkylamino moiety bonded to a sulfonyl group. Examples of an “alkylaminosulfonyl” group include CH₃NHS(O)₂— or CH₃CH₂CH₂NHS(O)₂—. The term “dialkylaminosulfonyl” denotes a straight-chain or branched dialkylamino moiety bonded to a sulfonyl group. Examples of a “dialkylaminosulfonyl” group include (CH₃)₂NS(O)₂— or (CH₃CH₂CH₂)₂NS(O)₂—.

The total number of carbon atoms in a substituent group is indicated by the “C_(i)-C_(j)” prefix where i and j are numbers from 1 to 14. For example, C₁-C₄ alkylsulfonyl designates methylsulfonyl through butylsulfonyl; C₂ alkoxyalkyl designates CH₃OCH₂—; C₃ alkoxyalkyl designates, for example, CH₃CH(OCH₃)—, CH₃OCH₂CH₂— or CH₃CH₂OCH₂—; and C₄ alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH₃CH₂CH₂OCH₂— and CH₃CH₂OCH₂CH₂—.

When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1, said substituents (when they exceed 1) are independently selected from the group of defined substituents, e.g., (R^(v))_(r), r is 1, 2, 3, 4 or 5 in U-1 of Exhibit 2. When a group contains a substituent which can be hydrogen, for example R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁸, R¹⁹ or R²⁰, then when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted. When a variable group is shown to be optionally attached to a position, for example (R^(v))_(r) in Q-29 of Exhibit 1 then hydrogen may be at the position even if not recited in the variable group definition. When one or more positions on a group are said to be “not substituted” or “unsubstituted”, then hydrogen atoms are attached to take up any free valency.

Unless otherwise indicated, a “ring” or “ring system” as a component of Formula 1 (e.g., substituent G) is carbocyclic or heterocyclic. The term “ring system” denotes two or more fused rings. The terms “bicyclic ring system” and “fused bicyclic ring system” denote a ring system consisting of two fused rings, in which either ring can be saturated, partially unsaturated, or fully unsaturated unless otherwise indicated. The term “ring member” refers to an atom or other moiety (e.g., C(═O), C(═S), S(O) or S(O)₂) forming the backbone of a ring or ring system.

The terms “carbocyclic ring”, “carbocycle” or “carbocyclic ring system” denote a ring or ring system wherein the atoms forming the ring backbone are selected only from carbon. Unless otherwise indicated, a carbocyclic ring can be a saturated, partially unsaturated, or fully unsaturated ring. When a fully unsaturated carbocyclic ring satisfies Hückel's rule, then said ring is also called an “aromatic ring”. “Saturated carbocyclic” refers to a ring having a backbone consisting of carbon atoms linked to one another by single bonds; unless otherwise specified, the remaining carbon valences are occupied by hydrogen atoms.

The terms “heterocyclic ring”, “heterocycle” or “heterocyclic ring system” denote a ring or ring system in which at least one atom forming the ring backbone is not carbon, e.g., nitrogen, oxygen or sulfur. Typically a heterocyclic ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs. Unless otherwise indicated, a heterocyclic ring can be a saturated, partially unsaturated, or fully unsaturated ring. When a fully unsaturated heterocyclic ring satisfies Hückel's rule, then said ring is also called a “heteroaromatic ring” or “aromatic heterocyclic ring”. Unless otherwise indicated, heterocyclic rings and ring systems can be attached through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.

“Aromatic” indicates that each of the ring atoms is essentially in the same plane and has a p-orbital perpendicular to the ring plane, and that (4n+2) π electrons, where n is a positive integer, are associated with the ring to comply with Hückel's rule. The term “aromatic ring system” denotes a carbocyclic or heterocyclic ring system in which at least one ring of the ring system is aromatic. The term “aromatic carbocyclic ring system” denotes a carbocyclic ring system in which at least one ring of the ring system is aromatic. The term “aromatic heterocyclic ring system” denotes a heterocyclic ring system in which at least one ring of the ring system is aromatic. The term “nonaromatic ring system” denotes a carbocyclic or heterocyclic ring system that may be fully saturated, as well as partially or fully unsaturated, provided that none of the rings in the ring system are aromatic. The term “nonaromatic carbocyclic ring system” denotes a carbocylcic ring system in which no ring in the ring system is aromatic. The term “nonaromatic heterocyclic ring system” denotes a heterocyclic ring system in which no ring in the ring system is aromatic.

As used herein, the following definitions shall apply unless otherwise indicated. The term “optionally substituted” is used interchangeably with the phrase “substituted or unsubstituted” or with the term “(un)substituted.” Unless otherwise indicated, an optionally substituted group may have a substituent at each substitutable position of the group, and each substitution is independent of the other.

When G is a 5- or 6-membered nitrogen-containing heterocyclic ring, it may be attached to the remainder of Formula 1 through any available carbon or nitrogen ring atom, unless otherwise described. When G is (among others) a 5- or 6-membered heterocyclic ring it may be saturated or unsaturated, optionally substituted with one or more substituents selected from a group of substituents as defined in the Summary of the Invention. Examples of a 5- or 6-membered unsaturated aromatic heterocyclic ring optionally substituted with from one or more substituents include the rings Q-1 through Q-60 illustrated in Exhibit 1 wherein R^(v) is any substituent as defined in the Summary of the Invention for R²¹ on carbon ring members or R²² on nitrogen ring members, and r is an integer from 0 to 4, limited by the number of available positions on each Q group. As Q-29, Q-30, Q-36, Q-37, Q-38, Q-39, Q-40, Q-41, Q-42 and Q-43 have only one available position, for these Q groups r is limited to the integers 0 or 1, and r being 0 means that the Q group is unsubstituted and a hydrogen is present at the position indicated by (R^(v))_(r).

Note that when G is a 5- or 6-membered saturated or unsaturated non-aromatic heterocyclic ring optionally substituted with one or more substituents selected from the group of substituents as defined in the Summary of the Invention for R²¹ one or two carbon ring members of the heterocycle can optionally be in the oxidized form of a carbonyl moiety.

Examples of a 5- or 6-membered saturated or non-aromatic unsaturated heterocyclic ring include the rings U-1 through U-36 as illustrated in Exhibit 2. Note that when the attachment point on the U group is illustrated as floating, the U group can be attached to the remainder of Formula 1 through any available carbon or nitrogen of the U group by replacement of a hydrogen atom. The optional substituents corresponding to R^(v) can be attached to any available carbon or nitrogen by replacing a hydrogen atom. For these U rings, r is typically an integer from 0 to 4, limited by the number of available positions on each U group.

Note that when G comprises a ring selected from U-29 through U-36, U² is selected from O, S or N. Note that when U² is N, the nitrogen atom can complete its valence by substitution with either H or the substituents corresponding to R^(v) as defined in the Summary of the Invention for U (i.e. R²²).

As noted above, G can be (among others) an 8-, 9- or 10-membered fused bicyclic ring system optionally substituted with one or more substituents selected from a group of substituents as defined in the Summary of the Invention (i.e. R²¹). Examples of 8-, 9- or 10-membered fused bicyclic ring system optionally substituted with from one or more substituents include the rings Q-81 through Q-123 illustrated in Exhibit 3 wherein R^(v) is any substituent as defined in the Summary of the Invention for G (i.e. R²¹ or R²²), and r is typically an integer from 0 to 4.

Although R^(v) groups are shown in the structures Q-1 through Q-60 and Q-81 through Q-123, it is noted that they do not need to be present since they are optional substituents. The nitrogen atoms that require substitution to fill their valence are substituted with H or R^(v). Note that when the attachment point between (R^(v))_(r) and the Q group is illustrated as floating, (R^(v))_(r) can be attached to any available carbon atom or nitrogen atom of the Q group. Note that when the attachment point on the Q group is illustrated as floating, the Q group can be attached to the remainder of Formula 1 through any available carbon or nitrogen of the Q group by replacement of a hydrogen atom. Note that some Q groups can only be substituted with less than 4 R^(v) groups (e.g., Q-1 through Q-5, Q-7 through Q-48, and Q-52 through Q-60).

As noted in the Summary of the Invention, R¹ and R² are taken together along with the atoms to which they are attached to make a 5-, 6- or 7-membered unsaturated, partially unsaturated or fully unsaturated ring along with members consisting of up to 2 oxygen atoms, 2 nitrogen atoms or 2 sulfur atoms or up to two —S(O)—, —S(O)₂—, —C(O)— groups. Besides the possibility of R¹ and R² being separate substituents, they may also be connected to form a ring fused to the ring to which they are attached. The fused ring can be a 5-, 6- or 7-membered ring including as ring members the two atoms shared with the ring to which the substituents are attached. The other 3, 4 or 5 ring members of the fused ring are provided by R¹ and R² substituents taken together. These other ring members can include up to 5 carbon atoms (as allowed by the ring size) and optionally up to 3 heteroatoms selected from up to 2 O, up to 2 S and up to 3 N. The fused ring is optionally substituted with up to 3 substituents as noted in the Summary of the Invention. Exhibit 4 provides, as illustrative examples, rings formed by R¹ and R² taken together. As these rings are fused with a ring of Formula 1, a portion of the Formula 1 ring is shown and the truncated lines represent the ring bonds of the Formula 1 ring. The rings depicted are fused to the two adjacent atoms of a ring as shown in Formula 1. The optional substituents (R^(v))_(r), are independently selected from the group consisting of halogen, cyano, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl and C₂-C₈ alkoxyalkyl; and phenyl optionally substituted with up to 5 substituents selected from cyano, nitro, halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₁-C₆ haloalkoxy; on carbon atom ring members. The optional substituents (R^(v))_(r), are independently selected from the group consisting of H and C₁-C₆ alkyl; and phenyl optionally substituted with up to 5 substituents selected from cyano, nitro, halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₁-C₆ haloalkoxy; on nitrogen ring members. Substituents are limited by the number of available positions on each T-ring. When the attachment point between (R^(v))_(r) and the T-ring is illustrated as floating, R^(v) may be bonded to any available T-ring carbon or nitrogen atom (as applicable). One skilled in the art recognizes that while r is nominally an integer from 0 to 3, some of the rings shown in Exhibit 4 have less than 3 available positions, and for these groups r is limited to the number of available positions. When “r” is 0 this means the ring is unsubstituted and hydrogen atoms are present at all available positions. If r is 0 and (R^(v))_(r) is shown attached to a particular atom, then hydrogen is attached to that atom. The nitrogen atoms that require substitution to fill their valence are substituted with H or R^(v). Furthermore, one skilled in the art recognizes that some of the rings shown in Exhibit 4 can form tautomers, and the particular tautomer depicted is representative of all the possible tautomers.

A wide variety of synthetic methods are known in the art to enable preparation of aromatic and nonaromatic heterocyclic rings and ring systems; for extensive reviews see the eight volume set of Comprehensive Heterocyclic Chemistry, A. R. Katritzky and C. W. Rees editors-in-chief, Pergamon Press, Oxford, 1984 and the twelve volume set of Comprehensive Heterocyclic Chemistry II, A. R. Katritzky, C. W. Rees and E. F. V. Scriven editors-in-chief, Pergamon Press, Oxford, 1996.

Compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers. The compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers or as an optically active form.

One skilled in the art will recognize that when A is A-1, A-2 or A-3, and the R³ variable is hydroxy or O⁻M⁺, then the resulting compound of Formula 1 can exist in either the “triketone” tautomer or the “di-keto enol” tautomer. Likewise, when A is A-1, A-2 or A-3, and the R³ variable is —SH, the resulting compound of Formula 1 can exist in either the the “di-keto thioketo” tautomer or the “di-keto thioenol” tautomer. In any of these cases and for the purposes of this invention both tautomeric combinations represent fully functional species of the present invention. For example, named species using the phrase “2-(1,3-cyclohexanedione)” is synonymous with the term “3-oxo-1-cyclohexen-1-yl”.

Compounds of Formula 1 typically exist in more than one form, and Formula 1 thus include all crystalline and non-crystalline forms of the compounds they represent. Non-crystalline forms include embodiments which are solids such as waxes and gums as well as embodiments which are liquids such as solutions and melts. Crystalline forms include embodiments which represent essentially a single crystal type and embodiments which represent a mixture of polymorphs (i.e. different crystalline types). The term “polymorph” refers to a particular crystalline form of a chemical compound that can crystallize in different crystalline forms, these forms having different arrangements and/or conformations of the molecules in the crystal lattice. Although polymorphs can have the same chemical composition, they can also differ in composition due the presence or absence of co-crystallized water or other molecules, which can be weakly or strongly bound in the lattice. Polymorphs can differ in such chemical, physical and biological properties as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate and biological availability. One skilled in the art will appreciate that a polymorph of a compound of Formula 1 can exhibit beneficial effects (e.g., suitability for preparation of useful formulations, improved biological performance) relative to another polymorph or a mixture of polymorphs of the same compound of Formula 1. Preparation and isolation of a particular polymorph of a compound of Formula 1 can be achieved by methods known to those skilled in the art including, for example, crystallization using selected solvents and temperatures.

One skilled in the art will appreciate that not all nitrogen-containing heterocycles can form N-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen-containing heterocycles which can form N-oxides. One skilled in the art will also recognize that tertiary amines can form N-oxides. Synthetic methods for the preparation of N-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane. These methods for the preparation of N-oxides have been extensively described and reviewed in the literature, see for example: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp 748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik in Comprehensive Heterocyclic Chemistry, vol. 3, pp 18-20, A. J. Boulton and A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keene in Advances in Heterocyclic Chemistry, vol. 43, pp 149-161, A. R. Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advances in Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J. Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G. Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A. R. Katritzky and A. J. Boulton, Eds., Academic Press.

One skilled in the art recognizes that because in the environment and under physiological conditions salts of chemical compounds are in equilibrium with their corresponding nonsalt forms, salts share the biological utility of the nonsalt forms. Thus a wide variety of salts of a compound of Formula 1 are useful for control of undesired vegetation (i.e. are agriculturally suitable). The salts of a compound of Formula 1 include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids. When a compound of Formula 1 contains an acidic moiety such as a carboxylic acid or phenol, salts also include those formed with organic or inorganic bases such as pyridine, triethylamine or ammonia, or amides, hydrides, hydroxides or carbonates of sodium, potassium, lithium, calcium, magnesium or barium. Accordingly, the present invention comprises compounds selected from Formula 1, N-oxides and agriculturally suitable salts thereof.

Embodiments of the present invention as described in the Summary of the Invention also include (where Formula 1 as used in the following Embodiments includes N-oxides and salts thereof):

Embodiment 1

A compound of Formula 1 wherein A is A-1, A-3, A-4, A-5 or A-6.

Embodiment 2

A compound of Embodiment 1 wherein A is A-1, A-3, A-5 or A-6.

Embodiment 3

A compound of Embodiment 2 wherein A is A-1, A-3 or A-5.

Embodiment 4

A compound of Embodiment 3 wherein A is A-1 or A-3.

Embodiment 5

A compound of Embodiment 4 wherein A is A-1.

Embodiment 6

A compound of Embodiment 4 wherein A is A-3.

Embodiment 7

A compound of Formula 1 or any one of Embodiments 1 through 5 wherein A is other than A-1.

Embodiment 8

A compound of Formula 1 or any one of Embodiments 1 through 7 wherein B¹ is C-1.

Embodiment 9

A compound of Formula 1 or any one of Embodiments 1 through 7 wherein B¹ is C-2.

Embodiment 10

A compound of Formula 1 or any one of Embodiments 1 through 9 wherein B² is C-3.

Embodiment 11

A compound of Formula 1 or any one of Embodiments 1 through 9 wherein B² is C-4.

Embodiment 12

A compound of Formula 1 or any one of Embodiments 1 through 11 wherein B³ is C-1.

Embodiment 13

A compound of Formula 1 or any one of Embodiments 1 through 11 wherein B³ is C-2.

Embodiment 14

A compound of Formula 1 or any one of Embodiments 1 through 13 wherein R¹ is phenyl, phenylsulfonyl, —W¹(phenyl), —W¹(S-phenyl), —W¹(SO₂-phenyl), —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each optionally substituted on ring members with up to five substituents selected from R²¹; or -G or —W²G; or cyano, hydroxy, amino, —C(═O)OH, —C(═O)NHCN, —C(═O)NHOH, —SO₂NH₂, —SO₂NHCN, —SO₂NHOH, —NHCHO, C₁-C₁₀ alkyl, C₂-C₁₀ alkenyl, C₂-C₁₀ alkynyl, C₁-C₁₀ haloalkyl, C₂-C₁₀ haloalkenyl, C₂-C₁₂ haloalkynyl, C₃-C₁₂ cycloalkyl, C₃-C₁₂ halocycloalkyl, C₄-C₁₄ alkylcycloalkyl, C₄-C₁₄ cycloalkylalkyl, C₆-C₁₈ cycloalkylcycloalkyl, C₄-C₁₄ halocycloalkylalkyl, C₅-C₁₆ alkylcycloalkylalkyl, C₃-C₁₂ cycloalkenyl, C₃-C₁₂ halocycloalkenyl, C₂-C₁₂ alkoxyalkyl, C₃-C₁₂ alkoxyalkenyl, C₄-C₁₄ alkylcycloalkyl, C₄-C₁₄ alkoxycycloalkyl, C₄-C₁₄ cycloalkoxyalkyl, C₅-C₁₄ cycloalkoxyalkoxyalkyl, C₃-C₁₄ alkoxyalkoxyalkyl, C₂-C₁₂ alkylthioalkyl, C₂-C₁₂ alkylsulfinylalkyl, C₂-C₁₂ alkylsulfonylalkyl, C₂-C₁₂ alkylaminoalkyl, C₃-C₁₄ dialkylaminoalkyl, C₂-C₁₂ haloalkylaminoalkyl, C₄-C₁₄ cycloalkylaminoalkyl, C₂-C₁₂ alkylcarbonyl, C₂-C₁₂ haloalkylcarbonyl, C₄-C₁₄ cycloalkylcarbonyl, C₂-C₁₂ alkoxycarbonyl, C₄-C₁₆ cycloalkoxycarbonyl, C₅-C₁₄ cycloalkylalkoxycarbonyl, C₂-C₁₂ alkylaminocarbonyl, C₃-C₁₄ dialkylaminocarbonyl, C₄-C₁₄ cycloalkylaminocarbonyl, C₂-C₉ cyanoalkyl, C₁-C₁₀ hydroxyalkyl, C₄-C₁₄ cycloalkenylalkyl, C₂-C₁₂ haloalkoxyalkyl, C₂-C₁₂ alkoxyhaloalkyl, C₂-C₁₂ haloalkoxyhaloalkyl, C₄-C₁₄ halocycloalkoxyalkyl, C₄-C₁₄ cycloalkenyloxyalkyl, C₄-C₁₄ halocycloalkenyloxyalkyl, C₃-C₁₄ dialkoxyalkyl, C₃-C₁₄ alkoxyalkylcarbonyl, C₃-C₁₄ alkoxycarbonylalkyl or C₂-C₁₂ haloalkoxycarbonyl.

Embodiment 15

A compound of Formula 1 or any one of Embodiments 1 through 14 wherein R¹ is phenyl, phenylsulfonyl, —W¹(phenyl), —W¹(S-phenyl), —W¹(SO₂-phenyl), —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each optionally substituted on ring members with up to five substituents selected from R²¹; or -G or —W²G; or cyano, hydroxy, amino, —C(═O)OH, —C(═O)NHCN, —C(═O)NHOH, —SO₂NH₂, —SO₂NHCN, —SO₂NHOH, —NHCHO, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₃-C₁₀ alkoxyalkenyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ alkoxycycloalkyl, C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈ alkylsulfonylalkyl, C₂-C₈ alkylaminoalkyl, C₃-C₁₀ dialkylaminoalkyl, C₂-C₈ haloalkylaminoalkyl, C₄-C₁₀ cycloalkylaminoalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈ alkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₅-C₁₂ cycloalkylalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₂-C₅ cyanoalkyl, C₁-C₆ hydroxyalkyl, C₄-C₁₀ cycloalkenylalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈ alkoxyhaloalkyl, C₂-C₈ haloalkoxyhaloalkyl, C₄-C₁₀ halocycloalkoxyalkyl, C₄-C₁₀ cycloalkenyloxyalkyl, C₄-C₁₀ halocycloalkenyloxyalkyl, C₃-C₁₀ dialkoxyalkyl, C₃-C₁₀ alkoxyalkylcarbonyl, C₃-C₁₀ alkoxycarbonylalkyl or C₂-C₈ haloalkoxycarbonyl.

Embodiment 16

A compound of Embodiment 15 wherein R¹ is phenyl, —W¹(phenyl), —W¹(S-phenyl), —W¹(SO₂-phenyl), —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each optionally substituted on ring members with up to five substituents selected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈ cycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₃-C₁₀ alkoxyalkenyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ alkoxycycloalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl or C₂-C₈ alkylsulfonylalkyl.

Embodiment 17

A compound of Embodiment 16 wherein R¹ is phenyl or —W¹(phenyl), each optionally substituted on ring members with up to two substituents selected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈ cycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl C₃-C₁₀ alkoxyalkenyl, C₄-C₁₀ alkylcycloalkyl or C₄-C₁₀ alkoxycycloalkyl.

Embodiment 18

A compound of Embodiment 17 wherein R¹ is phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 4-methylphenyl, 4-ethylphenyl, 2-methylphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 2,3-dimethylphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl.

Embodiment 19

A compound of Embodiment 18 wherein R¹ is phenyl, 4-ethylphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl.

Embodiment 20

A compound of Embodiment 19 wherein R¹ is phenyl, 3,4-dimethoxyphenyl or 5-chloro-2-methylphenyl.

Embodiment 21

A compound of Embodiment 20 wherein R¹ is phenyl.

Embodiment 22

A compound of Embodiment 19 wherein R¹ is 3,4-dimethoxyphenyl.

Embodiment 23

A compound of Embodiment 19 wherein R¹ is 5-chloro-2-methylphenyl.

Embodiment 24

A compound of Formula 1 or any one of Embodiments 1 through 21 wherein R¹ is other than phenyl.

Embodiment 25

A compound of Embodiment 17 wherein R¹ is -G or —W²G; C₁-C₆ alkyl, C₃-C₈ cycloalkyl, or C₂-C₈ alkoxyalkyl.

Embodiment 26

A compound of Embodiment 25 wherein R¹ is -G or —W²G.

Embodiment 27

A compound of Embodiment 26 wherein R¹ is C₁-C₆ alkyl, C₃-C₈ cycloalkyl, or C₂-C₈ alkoxyalkyl.

Embodiment 28

A compound of Embodiment 27 wherein R¹ is n-Pr, i-Pr, n-Bu, c-hexyl, c-heptyl, —CH₂CH₂OCH₃, —CH₂CH₂CH₂OCH₃ or —CH₂CH₂OCH₂CH₃.

Embodiment 29

A compound of Embodiment 28 wherein R¹ is n-Pr, c-hexyl, —CH₂CH₂OCH₃ or —CH₂CH₂CH₂OCH₃.

Embodiment 29a

A compound of Embodiment 29 wherein R¹ is n-Pr or —CH₂CH₂OCH₃.

Embodiment 29b

A compound of Embodiment 29 wherein R¹ is c-hexyl.

Embodiment 30

A compound of Formula 1 or any one of Embodiments 1 through 17 wherein W¹ is C₁-C₆ alkylene.

Embodiment 31

A compound of Embodiment 30 wherein W¹ is —CH₂—.

Embodiment 32

A compound of Formula 1 or any one of Embodiments 1 through 17, 25 or 26 wherein W² is —CH₂—.

Embodiment 33

A compound of Formula 1 or any one of Embodiments 1 through 32 wherein R² is phenyl or —W³(phenyl), each optionally substituted on ring members with up to five substituents selected from R²¹; or -G; C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₃-C₁₀ alkoxyalkenyl, C₄-C₁₀ cycloalkoxyalkyl, C₄-C₁₀ cycloalkoxylalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈ alkylsulfonylalkyl, C₂-C₈ alkylcarbonyl, C₄-C₁₀ cycloalkenylalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈ alkoxyhaloalkyl, C₂-C₈ haloalkoxyhaloalkyl, C₄-C₁₀ halocycloalkoxyalkyl, C₄-C₁₀ cycloalkenyloxyalkyl, C₄-C₁₀ halocycloalkenyloxyalkyl, C₃-C₁₀ dialkoxyalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy, C₂-C₆ alkynyloxy, C₃-C₆ haloalkynyloxy, C₂-C₈ alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy, C₂-C₈ haloalkylcarbonyloxy, C₄-C₁₀ cycloalkylcarbonyloxy, C₃-C₁₀ alkylcarbonylalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₃-C₈ trialkylsilyl, C₃-C₈ cycloalkenyloxy, C₃-C₈ halocycloalkenyloxy, C₂-C₈ haloalkoxyalkoxy, C₂-C₈ alkoxyhaloalkoxy, C₂-C₈ haloalkoxyhaloalkoxy, C₃-C₁₀ alkoxycarbonylalkoxy, C₂-C₈ alkyl(thiocarbonyl)oxy, C₃-C₈ cycloalkylsulfinyl or C₃-C₁₀ halotrialkylsilyl.

Embodiment 34

A compound of Embodiment 33 wherein R² is phenyl or —W³(phenyl), each optionally substituted on ring members with up to two substituents selected from R²¹; or -G or; or C₁-C₆ alkyl or C₃-C₈ cycloalkyl.

Embodiment 35

A compound of Embodiment 34 wherein R² is phenyl optionally substituted on ring members with up to two substituents selected from R²¹; or -G; or C₁-C₆ alkyl, C₃-C₈ cycloalkyl.

Embodiment 36

A compound of Embodiment 35 wherein R² is phenyl, 2-methylphenyl, 3-methylphenyl, 4-chlorophenyl, 3-fluorophenyl or 3,5-difluorophenyl.

Embodiment 36a

A compound of Embodiment 35 wherein R² is phenyl, 3-bromophenyl, 3-chlorophenyl, or 2-methylphenyl.

Embodiment 37

A compound of Embodiment 35 wherein R² is phenyl.

Embodiment 38

A compound of Formula 1 or any one of Embodiments 1 through 36 wherein R² is other than phenyl.

Embodiment 39

A compound of Embodiment 35 wherein R² is 3-thienyl or 2-thienyl.

Embodiment 40

A compound of Embodiment 35 wherein R² is n-propyl, n-butyl, or cyclopropyl.

Embodiment 41

A compound of Formula 1 or any one of Embodiments 1 through 13 wherein R¹ and R² are taken together along with the atoms to which they are attached to make a 6- or 7-membered unsaturated, partially unsaturated or fully unsaturated ring along with members consisting of up to 2 oxygen atoms, 2 nitrogen atoms or 2 sulfur atoms or up to two —S(O)—, —S(O)₂—, —C(O)— groups optionally substituted on carbon atom ring members selected from halogen, cyano, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl and C₂-C₈ alkoxyalkyl; and phenyl optionally substituted with up to 5 substituents selected from cyano, nitro, halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₁-C₆ haloalkoxy; and optionally substituted on nitrogen ring members selected from H and C₁-C₆ alkyl; and phenyl optionally substituted with up to 5 substituents selected from cyano, nitro, halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₁-C₆ haloalkoxy.

Embodiment 42

A compound of Embodiment 41 wherein R¹ and R² are taken together along with the atoms to which they are attached to make a 6- or 7-membered unsaturated, partially unsaturated or fully unsaturated ring along with members consisting of up to 1 oxygen atoms, 1 nitrogen atoms or 1 sulfur atoms or up to one —S(O)—, —S(O)₂—, —C(O)— groups optionally substituted on carbon atom ring members selected from halogen, cyano, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl and C₂-C₈ alkoxyalkyl; and optionally substituted on nitrogen ring members selected from H and C₁-C₆ alkyl.

Embodiment 43

A compound of Embodiment 42 wherein R¹ and R² are taken together along with the atoms to which they are attached to make a 7-membered partially unsaturated ring optionally substituted with halogen, cyano, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl or C₂-C₈ alkoxyalkyl on carbon atom ring members.

Embodiment 44

A compound of Embodiment 43 wherein R¹ and R² are taken together along with the atoms to which they are attached to make an unsubstituted 7-membered partially unsaturated ring.

Embodiment 45

A compound of Formula 1 or any one of Embodiments 1 through 34 wherein W³ is —CH₂—.

Embodiment 46

A compound of Formula 1 or any one of Embodiments 1 through 32 wherein W⁴ is —CH₂—.

Embodiment 47

A compound of Formula 1 or any one of Embodiments 1 through 46 wherein R³ is hydroxy, C₂-C₈ alkylcarbonyloxy, C₂-C₈ haloalkylcarbonyloxy, C₄-C₁₀ cycloalkylcarbonyloxy or C₃-C₁₀ alkylcarbonylalkoxy; or benzyloxy, phenyloxy, benzylcarbonyloxy, phenylcarbonyloxy, phenylsulfonyloxy or benzylsulfonyloxy, each optionally substituted on ring members with up to two substituents selected from R²¹.

Embodiment 48

A compound of Embodiment 47 wherein R³ is hydroxy, —O⁻M⁺ or C₂-C₈ alkylcarbonyloxy; or phenylsulfonyloxy optionally substituted with up to two substituents selected from R²¹.

Embodiment 49

A compound of Embodiment 48 wherein M⁺ is a sodium or potassium metal cation.

Embodiment 50

A compound of Embodiment 49 wherein R³ is hydroxy or C₂-C₈ alkylcarbonyloxy.

Embodiment 51

A compound of Embodiment 50 wherein R³ is hydroxy or —OC(═O)CH₂CH(CH₃)₂.

Embodiment 52

A compound of Formula 1 or any one of Embodiments 1, 7 and 14 through 51 wherein R⁴, R⁵, R⁶ and R⁷ are each independently H, or C₁-C₆ alkyl.

Embodiment 53

A compound of Formula 1 or any one of Embodiments 1, 7 and 14 through 52 wherein R⁸ is C₁-C₆ alkyl or C₃-C₈ cycloalkyl.

Embodiment 54

A compound of Embodiment 53 wherein R⁸ is CH₃, CH₂CH₃ or cyclopropyl.

Embodiment 55

A compound of Formula 1 or any one of Embodiments 1 through 3, 7 and 14 through 51 wherein R⁹ is C₁-C₆ alkyl.

Embodiment 56

A compound of Embodiment 55 wherein R⁹ is CH₂CH₃.

Embodiment 57

A compound of Formula 1 or any one of Embodiments 1 through 3, 7 and 14 through 51 wherein R¹⁰ is H, halogen or C₁-C₆ alkyl.

Embodiment 58

A compound of Embodiment 57 wherein R¹⁰ is H or CH₃.

Embodiment 59

A compound of Formula 1 or any one of Embodiments 1, 2, 8, 10 and 12 through 51 wherein R¹¹ is H or C₁-C₆ alkyl.

Embodiment 60

A compound of Embodiment 59 wherein R¹¹ is H.

Embodiment 61

A compound of Formula 1 or any one of Embodiments 1, 2, 8, 10 and 12 through 51 wherein R¹² is H, halogen, cyano, hydroxy, amino or C₁-C₆ alkyl.

Embodiment 62

A compound of Embodiment 61 wherein R¹² is H, halogen, cyano, C₁-C₆ alkyl or C₃-C₈ cycloalkyl.

Embodiment 63

A compound of Embodiment 62 wherein R¹² is CH₃, CH₂CH₃ or cyclopropyl.

Embodiment 64

A compound of Formula 1 or any one of Embodiments 7 and 15 through 51 wherein R¹³ is H, halogen, cyano or nitro.

Embodiment 65

A compound of Embodiment 64 wherein R¹³ is cyano or nitro.

Embodiment 66

A compound of Formula 1 or any one of Embodiments 1 through 65 wherein when instances of R¹⁴ and R¹⁸ are taken alone (i.e. R¹⁴ and R¹⁸ are not taken together as alkylene or alkenylene), then independently said instances of R¹⁴ and R¹⁸ are H or C₁-C₆ alkyl.

Embodiment 67

A compound of Embodiment 66 wherein when instances of R¹⁴ and R¹⁸ are taken alone, then independently said instances of R¹⁴ and R¹⁸ are H or CH₃.

Embodiment 68

A compound of Embodiment 68 wherein when instances of R¹⁴ and R¹⁸ are taken alone, then independently said instances of R¹⁴ and R¹⁸ are H.

Embodiment 69

A compound of Formula 1 or any one of Embodiments 1 through 68 wherein when instances of R¹⁴ and R¹⁸ are taken together, then said instances of R¹⁴ and R¹⁸ are taken together as —CH₂CH₂CH₂— or —CH═CHCH₂—.

Embodiment 70

A compound of Formula 1 or any one of Embodiments 1 through 68 wherein all instances of R¹⁴ and R¹⁸ are taken alone.

Embodiment 71

A compound of Formula 1 or any one of Embodiments 1 through 70 wherein independently each R¹⁵ and R¹⁹ is H or C₁-C₆ alkyl.

Embodiment 72

A compound of Embodiment 71 wherein independently each R¹⁵ and R¹⁹ is H or CH₃.

Embodiment 73

A compound of Embodiment 72 wherein independently each R¹⁵ and R¹⁹ is H.

Embodiment 73a

A compound of Embodiments 67 and 72 wherein each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is H or CH₃.

Embodiment 73b

A compound of Embodiment 73 wherein each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is H.

Embodiment 74

A compound of Formula 1 or any one of Embodiments 1 through 73 wherein R²⁰ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl or C₃-C₈ cycloalkyl.

Embodiment 75

A compound of Embodiment 74 wherein R²⁰ is H or CH₃.

Embodiment 76

A compound of Formula 1 or any one of Embodiments 1 through 4, 6, 10, 11 and 14 through 51 wherein T is —CH₂CH₂— or —CH═CH—.

Embodiment 77

A compound of Embodiment 76 wherein T is —CH₂CH₂—.

Embodiment 78

A compound of Formula 1 or any one of Embodiments 1 through 17 wherein each G is independently a 5- or 6-membered heterocyclic ring optionally substituted with up to five substituents selected from R²¹ on carbon ring members and R²² on nitrogen ring members.

Embodiment 79

A compound of Embodiment 78 wherein G is

r is 0, 1, 2 or 3.

Embodiment 80

A compound of Embodiment 79 wherein G is G-2, G-3, G-9, G-15, G-18, G-19 or G-20.

Embodiment 81

A compound of Embodiment 79 wherein when R¹ is G, then G is G-18, G-19 or G-20.

Embodiment 82

A compound of Embodiment 81 wherein when R¹ is G, then G is G-19 or G-20.

Embodiment 83

A compound of Embodiment 82 wherein when R¹ is G, then G is G-20.

Embodiment 84

A compound of Embodiment 82 wherein when R¹ is G, then G is G-19.

Embodiment 85

A compound of Embodiment 79 wherein when R² is G, then G is G-2, G-3 or G-15.

Embodiment 86

A compound of Embodiment 84 wherein when R² is G, then G is G-2 or G-3.

Embodiment 87

A compound of Embodiment 84 wherein when R² is G, then G is G-2.

Embodiment 88

A compound of Embodiment 84 wherein when R² is G, then G is G-3.

Embodiment 89

A compound of Formula 1 or any one of Embodiments 1 through 88 wherein each R²¹ is independently halogen, cyano, hydroxy, nitro, —CHO, —SH, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈ alkoxyhaloalkyl, C₂-C₅ cyanoalkyl, C₁-C₆ hydroxyalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy, C₂-C₈ alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl or C₃-C₈ cycloalkylsulfonyl.

Embodiment 90

A compound of Embodiment 91 wherein each R²¹ is independently halogen, nitro, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy or C₁-C₆ alkylthio.

Embodiment 91

A compound of Embodiment 92 wherein each R²¹ is independently fluorine, chlorine, bromine, CH₃, CF₃, OCH₃, OCF₃ or SCH₃.

Embodiment 92

A compound of Formula 1 or any one of Embodiments 1 through 91 wherein each R²² is independently C₁-C₆ alkyl or C₁-C₆ haloalkyl.

Embodiment 93

A compound of Embodiment 92 wherein each R²² is independently CH₃ or CH₂CF₃.

This invention also includes a herbicidal mixture comprising (a) a compound of Formula 1 and (b) at least one additional active ingredient selected from (b1) photosystem II inhibitors, (b2) AHAS inhibitors, (b3) ACCase inhibitors, (b4) auxin mimics and (b5) EPSP inhibitors.

Embodiment 94

A herbicidal mixture comprising (a) a compound of Formula 1 and (b) at least one additional active ingredient selected from (b1), (b2) and (b3).

Embodiment 95

A herbicidal mixture comprising (a) a compound of Formula 1 and (b) at least one additional active ingredient selected from (b1).

Embodiment 96

A herbicidal mixture of Embodiment 95 comprising (a) a compound of Formula 1 and (b) one additional active ingredient selected from the group consisting of ametryn, amicarbazone, atrazine, bentazon, bromacil, bromoxynil, chlorotoluron, dimethametryn, diuron, hexazinone, isoproturon, metribuzin, pyridate, simazine and terbutryn.

Embodiment 97

A herbicidal mixture of Embodiment 95 comprising (a) a compound of Formula 1; and (b) bromoxynil.

Embodiment 98

A herbicidal mixture of Embodiment 95 comprising (a) a compound of Formula 1; and (b) dimethametryn.

Embodiment 99

A herbicidal mixture comprising (a) a compound of Formula 1 and (b) diuron and hexazinone.

Combinations of Embodiments 1-93 are illustrated by:

Embodiment A

A compound of Formula 1 wherein

-   -   A is A-1, A-3, A-4, A-5 or A-6;     -   R¹ is phenyl, phenylsulfonyl, —W¹(phenyl), —W¹(S-phenyl),         —W¹(SO₂-phenyl), —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each         optionally substituted on ring members with up to five         substituents selected from R²¹; or -G or —W²G; or cyano,         hydroxy, amino, —C(═O)OH, —C(═O)NHCN, —C(═O)NHOH, —SO₂NH₂,         —SO₂NHCN, —SO₂NHOH, —NHCHO, C₁-C₁₀ alkyl, C₂-C₁₀ alkenyl, C₂-C₁₀         alkynyl, haloalkyl, C₂-C₁₀ haloalkenyl, C₂-C₁₂ haloalkynyl,         C₃-C₁₂ cycloalkyl, C₃-C₁₂ halocycloalkyl, C₄-C₁₄         alkylcycloalkyl, C₄-C₁₄ cycloalkylalkyl, C₆-C₁₈         cycloalkylcycloalkyl, C₄-C₁₄ halocycloalkylalkyl, C₅-C₁₆         alkylcycloalkylalkyl, C₃-C₁₂ cycloalkenyl, C₃-C₁₂         halocycloalkenyl, C₂-C₁₂ alkoxyalkyl, C₃-C₁₂ alkoxyalkenyl,         C₄-C₁₄ alkylcycloalkyl, C₄-C₁₄ alkoxycycloalkyl, C₄-C₁₄         cycloalkoxyalkyl, C₅-C₁₄ cycloalkoxyalkoxyalkyl, C₃-C₁₄         alkoxyalkoxyalkyl, C₂-C₁₂ alkylthioalkyl, C₂-C₁₂         alkylsulfinylalkyl, C₂-C₁₂ alkylsulfonylalkyl, C₂-C₁₂         alkylaminoalkyl, C₃-C₁₄ dialkylaminoalkyl, C₂-C₁₂         haloalkylaminoalkyl, C₄-C₁₄ cycloalkylaminoalkyl, C₂-C₁₂         alkylcarbonyl, C₂-C₁₂ haloalkylcarbonyl, C₄-C₁₄         cycloalkylcarbonyl, C₂-C₁₂ alkoxycarbonyl, C₄-C₁₆         cycloalkoxycarbonyl, C₅-C₁₄ cycloalkylalkoxycarbonyl, C₂-C₁₂         alkylaminocarbonyl, C₃-C₁₄ dialkylaminocarbonyl, C₄-C₁₄         cycloalkylaminocarbonyl, C₂-C₉ cyanoalkyl, C₁-C₁₀ hydroxyalkyl,         C₄-C₁₄ cycloalkenylalkyl, C₂-C₁₂ haloalkoxyalkyl, C₂-C₁₂         alkoxyhaloalkyl, C₂-C₁₂ haloalkoxyhaloalkyl, C₄-C₁₄         halocycloalkoxyalkyl, C₄-C₁₄ cycloalkenyloxyalkyl, C₄-C₁₄         halocycloalkenyloxyalkyl, C₃-C₁₄ dialkoxyalkyl, C₃-C₁₄         alkoxyalkylcarbonyl, C₃-C₁₄ alkoxycarbonylalkyl or C₂-C₁₂         haloalkoxycarbonyl;     -   W¹ is C₁-C₆ alkylene;     -   W² is —CH₂—;     -   R² is phenyl or —W³(phenyl), each optionally substituted on ring         members with up to five substituents selected from R²¹; or -G;         C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl,         C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈         halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl,         C₆-C₁₄ cycloalkylcycloalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂         alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈         halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₃-C₁₀ alkoxyalkenyl,         C₄-C₁₀ cycloalkoxyalkyl, C₄-C₁₀ cycloalkoxylalkoxyalkyl, C₃-C₁₀         alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈         alkylsulfonylalkyl, C₂-C₈ alkylsulfonylalkyl, C₂-C₈         alkylcarbonyl, C₄-C₁₀ cycloalkenylalkyl, C₂-C₈ haloalkoxyalkyl,         C₂-C₈ alkoxyhaloalkyl, C₂-C₈ haloalkoxyhaloalkyl, C₄-C₁₀         halocycloalkoxyalkyl, C₄-C₁₀ cycloalkenyloxyalkyl, C₄-C₁₀         halocycloalkenyloxyalkyl, C₃-C₁₀ dialkoxyalkyl, C₁-C₆ alkoxy,         C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy,         C₄-C₁₀ cycloalkylalkoxy, C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy,         C₂-C₆ alkynyloxy, C₃-C₆ haloalkynyloxy, C₂-C₈ alkoxyalkoxy,         C₂-C₈ alkylcarbonyloxy, C₂-C₈ haloalkylcarbonyloxy, C₄-C₁₀         cycloalkylcarbonyloxy, C₃-C₁₀ alkylcarbonylalkoxy, C₁-C₆         alkylthio, C₁-C₆ haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆         alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl,         C₁-C₆ haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₃-C₈         trialkylsilyl, C₃-C₈ cycloalkenyloxy, C₃-C₈ halocycloalkenyloxy,         C₂-C₈ haloalkoxyalkoxy, C₂-C₈ alkoxyhaloalkoxy, C₂-C₈         haloalkoxyhaloalkoxy, C₃-C₁₀ alkoxycarbonylalkoxy, C₂-C₈         alkyl(thiocarbonyl)oxy, C₃-C₈ cycloalkylsulfinyl or C₃-C₁₀         halotrialkylsilyl;     -   W³ is —CH₂—;     -   W⁴ is —CH₂—;     -   R¹ and R² are taken together along with the atoms to which they         are attached to make a 6- or 7-membered unsaturated, partially         unsaturated or fully unsaturated ring along with members         consisting of up to 2 oxygen atoms, 2 nitrogen atoms or 2 sulfur         atoms or up to two —S(O)—, —S(O)₂—, —C(O)— groups optionally         substituted on carbon atom ring members selected from halogen,         cyano, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆         haloalkyl, C₃-C₈ cycloalkyl and C₂-C₈ alkoxyalkyl; and phenyl         optionally substituted with up to 5 substituents selected from         cyano, nitro, halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₁-C₆         haloalkoxy; and optionally substituted on nitrogen ring members         selected from H and C₁-C₆ alkyl; and phenyl optionally         substituted with up to 5 substituents selected from cyano,         nitro, halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₁-C₆ haloalkoxy;     -   R³ is hydroxy, C₂-C₈ alkylcarbonyloxy, C₂-C₈         haloalkylcarbonyloxy, C₄-C₁₀ cycloalkylcarbonyloxy or C₃-C₁₀         alkylcarbonylalkoxy; or benzyloxy, phenyloxy, benzylcarbonyloxy,         phenylcarbonyloxy, phenylsulfonyloxy or benzylsulfonyloxy, each         optionally substituted on ring members with up to two         substituents selected from R²¹;     -   M⁺ is a sodium or potassium metal cation;     -   R⁹ is C₁-C₆ alkyl;     -   R¹⁰ is H, halogen or C₁-C₆ alkyl;     -   R¹¹ is H or C₁-C₆ alkyl;     -   R¹² is H, halogen, cyano, hydroxy, amino or C₁-C₆ alkyl;     -   R¹³ is cyano or nitro;     -   each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is H or CH₃;     -   R¹⁴ and R¹⁸ are taken together as —CH₂CH₂CH₂— or —CH═CHCH₂—;     -   R²⁰ is H or CH₃;     -   T is —CH₂CH₂— or —CH═CH—;     -   each G is G-1 through G-20 (as depicted in Embodiment 79);     -   r is 0, 1, 2 or 3;     -   each R²¹ is independently halogen, cyano, hydroxy, nitro, —CHO,         —SH, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl,         C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈         halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl,         C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl,         C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈         alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈ alkoxyhaloalkyl,         C₂-C₅ cyanoalkyl, C₁-C₆ hydroxyalkyl, C₁-C₆ alkoxy, C₁-C₆         haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀         cycloalkylalkoxy, C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy, C₂-C₈         alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy, C₁-C₆ alkylthio, C₁-C₆         haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆         haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl         or C₃-C₈ cycloalkylsulfonyl; and     -   each R²² is independently C₁-C₆ alkyl or C₁-C₆ haloalkyl.

Embodiment B

A compound of Embodiment A wherein

-   -   X is CH;     -   A is A-3 or A-5;     -   B² is C-3;     -   R¹ is phenyl, —W¹(phenyl), —W¹(S-phenyl), —W¹(SO₂-phenyl),         —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each optionally         substituted on ring members with up to five substituents         selected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl,         C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈         cycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl,         C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl,         C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl or C₂-C₈         alkylsulfonylalkyl;     -   R² is phenyl or —W³(phenyl), each optionally substituted on ring         members with up to two substituents selected from R²¹; or C₁-C₆         alkyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl, C₁-C₆ alkoxy, C₁-C₆         alkylthio or C₁-C₆ alkylsulfonyl;     -   R³ is hydroxy or —O⁻M⁺; or phenylsulfonyloxy optionally         substituted on ring members with up to two substituents selected         from R²¹;     -   R⁹ is CH₂CH₃;     -   R¹⁰ is H or CH₃;     -   W¹ is —CH₂—;     -   W³ is —CH₂—;     -   G is G-13, G-14, G-15, G-16 or G-17; and     -   each R²¹ is independently halogen, nitro, C₁-C₆ alkyl, C₁-C₆         haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy or C₁-C₆ alkylthio.

Embodiment C

A compound of Embodiment A wherein

-   -   A is A-1, A-3 or A-5;     -   B¹ is C-1;     -   B² is C-3;     -   B³ is C-1;     -   R¹ is phenyl, —W¹(phenyl), —W¹(S-phenyl), —W¹(SO₂-phenyl),         —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each optionally         substituted on ring members with up to five substituents         selected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl,         C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈         cycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl,         C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl,         C₃-C₁₀ alkoxyalkenyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀         alkoxycycloalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈         alkylthioalkyl, C₂-C₁₂ alkylsulfonylalkyl or C₂-C₈         alkylsulfonylalkyl;     -   W¹ is —CH₂—;     -   R² is phenyl or —W³(phenyl), each optionally substituted on ring         members with up to two substituents selected from R²¹; or -G or;         or C₁-C₆ alkyl or C₃-C₈ cycloalkyl;     -   R¹ and R² are taken together along with the atoms to which they         are attached to make an unsubstituted 7-membered partially         unsaturated ring;     -   R³ is hydroxy or C₂-C₈ alkylcarbonyloxy;     -   R⁹ is CH₂CH₃;     -   R¹⁰ is H or CH₃;     -   G is G-2, G-3, G-9, G-15, G-18, G-19 or G-20; and     -   R²¹ is independently halogen, nitro, C₁-C₆ alkyl, C₁-C₆         haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy or C₁-C₆ alkylthio.

Embodiment D

A compound of Embodiment C wherein

-   -   A is A-1 or A-3;     -   R¹ is phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl,         2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 4-methylphenyl,         4-ethylphenyl, 2-methylphenyl, 3-methoxyphenyl, 4-methoxyphenyl,         3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 2,3-dimethylphenyl,         3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or         5-chloro-2-methylphenyl;     -   R² is phenyl, 2-methylphenyl, 3-methylphenyl, 3-bromophenyl,         3-chlorophenyl, 4-chlorophenyl, 3-fluorophenyl or         3,5-difluorophenyl;     -   R³ is hydroxy or —OC(═O)CH₂CH(CH₃)₂;     -   each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is H or CH₃; and     -   T is —CH₂CH₂—.

Embodiment E

A compound of Embodiment D wherein

-   -   A is A-1;     -   R¹ is phenyl, 4-ethylphenyl, 4-methoxyphenyl,         3,5-dimethylphenyl, 3,4-dimethoxyphenyl,         3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or         5-chloro-2-methylphenyl;     -   R² is phenyl, 3-chlorophenyl, or 2-methylphenyl;     -   R³ is hydroxy or —OC(═O)CH₂CH(CH₃)₂; and     -   each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is H.

Embodiment F

A compound of Embodiment C wherein

-   -   A is A-3;     -   R¹ is n-Pr or —CH₂CH₂OCH₃;     -   R² is phenyl, 2-methylphenyl, 3-methylphenyl, 4-chlorophenyl,         3-fluorophenyl or 3,5-difluorophenyl;     -   R³ is hydroxy; and     -   each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is H.

Embodiment G

A compound of Embodiment C wherein

-   -   A is A-1;     -   R¹ is -G or —W²G; C₁-C₆ alkyl, C₃-C₈ cycloalkyl, or C₂-C₈         alkoxyalkyl;     -   G is G-19 or G-20;     -   R² is phenyl, 2-methylphenyl, 3-methylphenyl, 4-chlorophenyl,         3-fluorophenyl or 3,5-difluorophenyl;     -   R³ is hydroxy; and     -   each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is H.

Embodiment H

A compound of Embodiment C wherein

-   -   A is A-1;     -   R¹ is n-Pr, c-hexyl, —CH₂CH₂OCH₃ or —CH₂CH₂CH₂OCH₃;     -   R² is 3-thienyl or 2-thienyl;     -   R³ is hydroxy; and     -   each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is H.

Specific embodiments include a compound of Formula 1 selected from:

-   5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2,3-diphenyl-4(3H)-pyrimidinone     (Compound 2), -   5-[(2-hydroxy-6-oxo-1-cyclohexane-1-yl)carbonyl]-3-(3-methoxypropyl)-2-(3-methylphenyl)-4(3H)-pyrimidinone     (Compound 118), -   5-[2-hydroxy-6-oxo-cyclohexen-1-yl)carbonyl]-3-(2-methoxyethyl)-2-(3-thienyl)-4(3H)-pyrimidinone     (Compound 97), -   5-[2-hydroxy-6-oxo-cyclohexen-1-yl)carbonyl]-3-(4-methoxyphenyl)-2-phenyl-4(3H)-pyrimidinone     (Compound 4), -   5-[2-hydroxy-6-oxo-cyclohexen-1-yl)carbonyl]-3-(3-methoxypropyl)-2-phenyl-4(3H)-pyrimidinone     (Compound 81) and -   3-cyclohexyl-5-[(2-hydroxy-6-oxo-cyclohexen-1-yl)carbonyl]-2-phenyl-4(3H)-pyrimidinone     (Compound 128).

Embodiments of the present invention as described in the Summary of the Invention also include (where Formula 1Q from the Summary of the Invention as used in the following Embodiments includes N-oxides and salts thereof):

Embodiment 1Q

A compound of Formula 1Q wherein A′ is A′-1, A′-3 or A′-5.

Embodiment 2Q

A compound of Embodiment 2Q wherein A′ is A′-1 or A′-3.

Embodiment 3Q

A compound of Embodiment 3Q wherein A′ is A′-1.

Embodiment 4Q

A compound of Embodiment 4Q wherein A′ is A′-3.

Embodiment 5Q

A compound of Formula 1Q or any one of Embodiments 1Q through 4Q wherein B¹ is C-1.

Embodiment 6Q

A compound of Formula 1Q or any one of Embodiments 1Q through 4Q wherein B¹ is C-2.

Embodiment 7Q

A compound of Formula 1Q or any one of Embodiments 1Q through 6Q wherein B² is C-3.

Embodiment 8Q

A compound of Formula 1Q or any one of Embodiments 1Q through 9Q wherein B² is C-4.

Embodiment 9Q

A compound of Formula 1Q or any one of Embodiments 1Q through 8Q wherein B³ is C-1.

Embodiment 10Q

A compound of Formula 1Q or any one of Embodiments 1Q through 8Q wherein B³ is C-2.

Embodiment 11Q

A compound of Formula 1Q or any one of Embodiments 1Q through 10Q wherein R¹ is phenyl, —W¹(phenyl), —W¹(S-phenyl), —W¹(SO₂-phenyl), —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each optionally substituted on ring members with up to five substituents selected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈ cycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₃-C₁₀ alkoxyalkenyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ alkoxycycloalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₁₂ alkylsulfinylalkyl or C₂-C₈ alkylsulfonylalkyl.

Embodiment 12Q

A compound of Embodiment 11Q wherein R¹ is phenyl or —W¹(phenyl), each optionally substituted on ring members with up to two substituents selected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈ cycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl C₃-C₁₀ alkoxyalkenyl, C₄-C₁₀ alkylcycloalkyl or C₄-C₁₀ alkoxycycloalkyl.

Embodiment 13Q

A compound of Embodiment 12Q wherein R¹ is phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 4-methylphenyl, 4-ethylphenyl, 2-methylphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 2,3-dimethylphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl.

Embodiment 14Q

A compound of Embodiment 13Q wherein R¹ is phenyl, 4-ethylphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl. Embodiment 15Q. A compound of Embodiment 14Q wherein R¹ is phenyl, 3,4-dimethoxyphenyl or 5-chloro-2-methylphenyl.

Embodiment 16Q

A compound of Embodiment 15Q wherein R¹ is phenyl.

Embodiment 17Q

A compound of Embodiment 14Q wherein R¹ is 3,4-dimethoxyphenyl.

Embodiment 18Q

A compound of Embodiment 14Q wherein R¹ is 5-chloro-2-methylphenyl.

Embodiment 19Q

A compound of Formula 1Q or any one of Embodiments 1 through 16Q wherein R¹ is other than phenyl.

Embodiment 20Q

A compound of Embodiment 11Q wherein R¹ is -G or —W²G; C₁-C₆ alkyl, C₃-C₈ cycloalkyl, or C₂-C₈ alkoxyalkyl.

Embodiment 21Q

A compound of Embodiment 20Q wherein R¹ is -G or —W²G.

Embodiment 22Q

A compound of Embodiment 20Q wherein R¹ is C₁-C₆ alkyl, C₃-C₈ cycloalkyl or C₂-C₈ alkoxyalkyl.

Embodiment 23Q

A compound of Embodiment 22Q wherein R¹ is n-Pr, i-Pr, n-Bu, c-hexyl, —CH₂CH₂OCH₃, —CH₂CH₂CH₂OCH₃ or —CH₂CH₂OCH₂CH₃.

Embodiment 24Q

A compound of Embodiment 23Q wherein R¹ is n-Pr, c-hexyl, —CH₂CH₂OCH₃ or —CH₂CH₂CH₂OCH₃.

Embodiment 25Q

A compound of Formula 1Q or any one of Embodiments 1Q through 12Q wherein W¹ is C₁-C₆ alkylene.

Embodiment 26Q

A compound of Embodiment 25Q wherein W¹ is —CH₂—.

Embodiment 27Q

A compound of Formula 1Q or any one of Embodiments 1Q through 12Q, 20Q or 21Q wherein W² is —CH₂—.

Embodiment 28Q

A compound of Formula 1Q or any one of Embodiments Embodiment 1Q through 27Q wherein R² is phenyl or —W³(phenyl), each optionally substituted on ring members with up to two substituents selected from R²¹; or -G or; or C₁-C₆ alkyl or C₃-C₈ cycloalkyl.

Embodiment 29Q

A compound of Embodiment 28Q wherein R² is phenyl optionally substituted on ring members with up to two substituents selected from R²¹; or -G; or C₁-C₆ alkyl, C₃-C₈ cycloalkyl.

Embodiment 30Q

A compound of Embodiment 29Q wherein R² is phenyl, 2-methylphenyl, 3-methylphenyl, 3-bromophenyl, 3-chlorophenyl, 4-chlorophenyl, 3-fluorophenyl or 3,5-difluorophenyl.

Embodiment 31Q

A compound of Embodiment 30Q wherein R² is phenyl.

Embodiment 32Q

A compound of Formula 1Q or any one of Embodiments 1Q through 30Q wherein R² is other than phenyl.

Embodiment 33Q

A compound of Embodiment 32Q wherein R² is 3-thienyl or 2-thienyl.

Embodiment 34Q

A compound of Embodiment 33Q wherein R² is n-propyl, n-butyl, or cyclopropyl.

Embodiment 35Q

A compound of Formula 1Q or any one of Embodiments 1Q through 28Q wherein W³ is —CH₂—.

Embodiment 36Q

A compound of Formula 1Q or any one of Embodiments 1Q through 3Q, 7Q and 14Q through 51Q wherein R⁹ is C₁-C₆ alkyl.

Embodiment 37Q

A compound of Formula 1Q or any one of Embodiments 1Q or 11Q through 36Q wherein R⁹ is CH₂CH₃.

Embodiment 38Q

A compound of Formula 1Q or any one of Embodiments 1Q or 11Q through 36Q wherein R¹⁰ is H, halogen or C₁-C₆ alkyl.

Embodiment 39Q

A compound of Embodiment 38Q wherein R¹⁰ is H or CH₃.

Embodiment 40Q

A compound of Formula 1Q or any one of Embodiments 1Q through 39Q wherein when instances of R¹⁴ and R¹⁸ are taken alone (i.e. R¹⁴ and R¹⁸ are not taken together as alkylene or alkenylene), then independently said instances of R¹⁴ and R¹⁸ are H or C₁-C₆ alkyl.

Embodiment 41Q

A compound of Embodiment 40Q wherein when instances of R¹⁴ and R¹⁸ are taken alone, then independently said instances of R¹⁴ and R¹⁸ are H or CH₃.

Embodiment 42Q

A compound of Embodiment 41Q wherein when instances of R¹⁴ and R¹⁸ are taken alone, then independently said instances of R¹⁴ and R¹⁸ are H.

Embodiment 43Q

A compound of Formula 1Q or any one of Embodiments 1Q through 42Q wherein independently each R¹⁵ and R¹⁹ is H or CH₃.

Embodiment 44Q

A compound of Embodiment 43Q wherein independently each R¹⁵ and R¹⁹ is H.

Embodiment 45Q

A compound of Formula 1Q or any one of Embodiments 1Q through 44Q wherein R²⁰ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl or C₃-C₈ cycloalkyl.

Embodiment 46Q

A compound of Embodiment 45Q wherein R²⁰ is H or CH₃.

Embodiment 47Q

A compound of Formula 1Q or any one of Embodiments 1Q, 2Q, 4Q, 7Q, 8Q and 11Q through 46Q wherein T is —CH₂CH₂— or —CH═CH—.

Embodiment 48Q

A compound of Embodiment 47Q wherein T is —CH₂CH₂—.

Embodiment 49Q

A compound of Formula 1Q or any one of Embodiments 1Q through 48Q wherein G is G-2, G-3, G-9, G-15, G-18, G-19 or G-20 (as depicted in Embodiment 79).

Embodiment 50Q

A compound of Embodiment 49Q wherein when R¹ is G, then G is G-19 or G-20.

Embodiment 51Q

A compound of Embodiment 50Q wherein when R¹ is G, then G is G-19.

Embodiment 52Q

A compound of Embodiment 50Q wherein when R¹ is G, then G is G-20.

Embodiment 53Q

A compound of Embodiment 49Q wherein when R² is G, then G is G-2, G-3 or G-15.

Embodiment 54Q

A compound of Embodiment 53Q wherein when R² is G, then G is G-2.

Embodiment 55Q

A compound of Embodiment 53Q wherein when R² is G, then G is G-3.

Embodiment 56Q

A compound of Formula 1Q or any one of Embodiments 1Q through 55Q wherein each R²¹ is independently halogen, nitro, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy or C₁-C₆ alkylthio.

Embodiment 57Q

A compound of Embodiment 56Q wherein each R²¹ is independently fluorine, chlorine, bromine, CH₃, CF₃, OCH₃, OCF₃ or SCH₃.

Embodiment 58Q

A compound of Formula 1Q or any one of Embodiments 1Q through 57Q wherein each R²² is independently C₁-C₆ alkyl or C₁-C₆ haloalkyl.

Embodiment 59Q

A compound of Embodiment 58Q wherein each R²² is independently CH₃ or CH₂CF₃.

Embodiments of the present invention as described in the Summary of the Invention also include (where Formula 1R from the Summary of the Invention as used in the following Embodiments include N-oxides and salts thereof):

Embodiment 1R

A compound of Formula 1R wherein R¹ is phenyl, —W¹(phenyl), —W¹(S-phenyl), —W¹(SO₂-phenyl), —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each optionally substituted on ring members with up to five substituents selected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈ cycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₃-C₁₀ alkoxyalkenyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ alkoxycycloalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₁₂ alkylsulfinylalkyl or C₂-C₈ alkylsulfonylalkyl.

Embodiment 2R

A compound of Embodiment 1R wherein R¹ is phenyl or —W¹(phenyl), each optionally substituted on ring members with up to two substituents selected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈ cycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₃-C₁₀ alkoxyalkenyl, C₄-C₁₀ alkylcycloalkyl or C₄-C₁₀ alkoxycycloalkyl.

Embodiment 3R

A compound of Embodiment 2R wherein R¹ is phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 4-methylphenyl, 4-ethylphenyl, 2-methylphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 2,3-dimethylphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl.

Embodiment 4R

A compound of Embodiment 3R wherein R¹ is phenyl, 4-ethylphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl.

Embodiment 5R

A compound of Embodiment 4R wherein R¹ is phenyl, 3,4-dimethoxyphenyl or 5-chloro-2-methylphenyl.

Embodiment 6R

A compound of Embodiment 5R wherein R¹ is phenyl.

Embodiment 7R

A compound of Embodiment 4R wherein R¹ is 3,4-dimethoxyphenyl.

Embodiment 8R

A compound of Embodiment 4R wherein R¹ is 5-chloro-2-methylphenyl.

Embodiment 9R

A compound of Formula 1R or any one of Embodiments 1R through 8R wherein R¹ is other than phenyl.

Embodiment 10R

A compound of Formula 1R or any one of Embodiments 1R and 2R R wherein R¹ is -G or —W²G; C₁-C₆ alkyl, C₃-C₈ cycloalkyl, or C₂-C₈ alkoxyalkyl.

Embodiment 11R

A compound of Embodiment 10R wherein R¹ is -G or —W²G.

Embodiment 12R

A compound of Embodiment 10R wherein R¹ is C₁-C₆ alkyl, C₃-C₈ cycloalkyl, or C₂-C₈ alkoxyalkyl.

Embodiment 13R

A compound of Embodiment 12R wherein R¹ is n-Pr, i-Pr, n-Bu, c-hexyl, —CH₂CH₂OCH₃, —CH₂CH₂CH₂OCH₃ or —CH₂CH₂OCH₂CH₃.

Embodiment 14R

A compound of Embodiment 13R wherein R¹ is n-Pr, c-hexyl, —CH₂CH₂OCH₃ or —CH₂CH₂CH₂OCH₃.

Embodiment 15R

A compound of Formula 1R or any one of Embodiments 1R and 2R wherein W¹ is C₁-C₆ alkylene.

Embodiment 16R

A compound of Embodiment 15R wherein W¹ is —CH₂—.

Embodiment 17R

A compound of Formula 1R or any one of Embodiments 1R, 2R 10R and 11R wherein W² is —CH₂—.

Embodiment 18R

A compound of Formula 1R or any one of Embodiments Embodiment 1R through 17R wherein R² is phenyl or —W³(phenyl), each optionally substituted on ring members with up to two substituents selected from R²¹; or -G or; or C₁-C₆ alkyl or C₃-C₈ cycloalkyl.

Embodiment 19R

A compound of Embodiment 18R wherein R² is phenyl optionally substituted on ring members with up to two substituents selected from R²¹; or -G; or C₁-C₆ alkyl or C₃-C₈ cycloalkyl.

Embodiment 20R

A compound of Embodiment 19R wherein R² is phenyl, 2-methylphenyl, 3-methylphenyl, 3-bromophenyl, 3-chlorophenyl, 4-chlorophenyl, 3-fluorophenyl or 3,5-difluorophenyl.

Embodiment 21R

A compound of Embodiment 20R wherein R² is phenyl.

Embodiment 22R

A compound of Formula 1R or any one of Embodiments 1R through 21R wherein R² is other than phenyl.

Embodiment 23R

A compound of Embodiment 22R wherein R² is 3-thienyl or 2-thienyl.

Embodiment 24R

A compound of Embodiment 23R wherein R² is n-propyl, n-butyl, or cyclopropyl.

Embodiment 25R

A compound of Formula 1R or any one of Embodiments 1R through 18R wherein W³ is —CH₂—.

Embodiment 26R

A compound of Formula 1R or any one of Embodiments 1R through 25R wherein G is G-2, G-3, G-9, G-15, G-18, G-19 or G-20 (as depicted in Embodiment 79).

Embodiment 27R

A compound of Embodiment 26R wherein when R¹ is G, then G is G-19 or G-20.

Embodiment 28R

A compound of Embodiment 27R wherein when R¹ is G, then G is G-19.

Embodiment 29R

A compound of Embodiment 28R wherein when R¹ is G, then G is G-20.

Embodiment 30R

A compound of Embodiment 26R wherein when R² is G, then G is G-2, G-3 or G-15.

Embodiment 31R

A compound of Embodiment 30R wherein when R² is G, then G is G-2.

Embodiment 32R

A compound of Embodiment 31R wherein when R² is G, then G is G-3.

Embodiment 33R

A compound of Formula 1R or any one of Embodiments 1R through 32R wherein each R²¹ is independently halogen, nitro, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy or C₁-C₆ alkylthio.

Embodiment 34R

A compound of Embodiment 33R wherein each R²¹ is independently fluorine, chlorine, bromine, CH₃, CF₃, OCH₃, OCF₃ or SCH₃.

Embodiment 35R

A compound of Formula 1R or any one of Embodiments 1R through 32R wherein each R²² is independently C₁-C₆ alkyl or C₁-C₆ haloalkyl.

Embodiment 36R

A compound of Embodiment 35R wherein each R²² is independently CH₃ or CH₂CF₃.

Embodiments of the present invention as described in the Summary of the Invention also include (where Formula 1S from the Summary of the Invention as used in the following Embodiments includes N-oxides and salts thereof):

Embodiment 1S

A compound of Formula 1S wherein R¹ is phenyl, —W¹(phenyl), —W¹(S-phenyl), —W¹(SO₂-phenyl), —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each optionally substituted on ring members with up to five substituents selected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈ cycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₃-C₁₀ alkoxyalkenyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ alkoxycycloalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₁₂ alkylsulfinylalkyl or C₂-C₈ alkylsulfonylalkyl.

Embodiment 2S

A compound of Embodiment 1S wherein R¹ is phenyl or —W¹(phenyl), each optionally substituted on ring members with up to two substituents selected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈ cycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₃-C₁₀ alkoxyalkenyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ alkoxycycloalkyl.

Embodiment 3S

A compound of Embodiment 2S wherein R¹ is phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 4-methylphenyl, 4-ethylphenyl, 2-methylphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 2,3-dimethylphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl.

Embodiment 4S

A compound of Embodiment 3S wherein R¹ is phenyl, 4-ethylphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl.

Embodiment 5S

A compound of Embodiment 4S wherein R¹ is phenyl, 3,4-dimethoxyphenyl or 5-chloro-2-methylphenyl.

Embodiment 6S

A compound of Embodiment 5S wherein R¹ is phenyl.

Embodiment 7S

A compound of Embodiment 4S wherein R¹ is 3,4-dimethoxyphenyl.

Embodiment 8S

A compound of Embodiment 4S wherein R¹ is 5-chloro-2-methylphenyl.

Embodiment 9S

A compound of Formula 1S or any one of Embodiments 1S through 8S wherein R¹ is other than phenyl.

Embodiment 10S

A compound of Formula 1S or any one of Embodiments 15 and 2S wherein R¹ is -G or —W²G; C₁-C₆ alkyl, C₃-C₈ cycloalkyl, or C₂-C₈ alkoxyalkyl.

Embodiment 11S

A compound of Embodiment 10S wherein R¹ is -G or —W²G.

Embodiment 12S

A compound of Embodiment 10S wherein R¹ is C₁-C₆ alkyl, C₃-C₈ cycloalkyl, or C₂-C₈ alkoxyalkyl.

Embodiment 13S

A compound of Embodiment 12S wherein R¹ is n-Pr, i-Pr, n-Bu, c-hexyl, —CH₂CH₂OCH₃, —CH₂CH₂CH₂OCH₃ or —CH₂CH₂OCH₂CH₃.

Embodiment 14S

A compound of Embodiment 13S wherein R¹ is n-Pr, c-hexyl, —CH₂CH₂OCH₃ or —CH₂CH₂CH₂OCH₃.

Embodiment 15S

A compound of Formula 1S or any one of Embodiments 15 and 2S wherein W¹ is C₁-C₆ alkylene.

Embodiment 16S

A compound of Embodiment 15S wherein W¹ is —CH₂—.

Embodiment 17S

A compound of Formula 15 or any one of Embodiments 1S, 2S 10S and 11S wherein W² is —CH₂—.

Embodiment 18S

A compound of Formula 1s or any one of Embodiments Embodiment 1S through 17S wherein R² is phenyl or —W³(phenyl), each optionally substituted on ring members with up to two substituents selected from R²¹; or -G or; or C₁-C₆ alkyl or C₃-C₈ cycloalkyl.

Embodiment 19S

A compound of Embodiment 18S wherein R² is phenyl optionally substituted on ring members with up to two substituents selected from R²¹; or -G; or C₁-C₆ alkyl, C₃-C₈ cycloalkyl.

Embodiment 20S

A compound of Embodiment 19S wherein R² is phenyl, 2-methylphenyl, 3-methylphenyl, 3-bromophenyl, 3-chlorophenyl, 4-chlorophenyl, 3-fluorophenyl or 3,5-difluorophenyl.

Embodiment 21S

A compound of Embodiment 20S wherein R² is phenyl.

Embodiment 22S

A compound of Formula 1S or any one of Embodiments 1S through 21S wherein R² is other than phenyl.

Embodiment 23S

A compound of Embodiment 22S wherein R² is 3-thienyl or 2-thienyl.

Embodiment 24S

A compound of Embodiment 23S wherein R² is n-propyl, n-butyl, or cyclopropyl.

Embodiment 25S

A compound of Formula 1S or any one of Embodiments 15 through 18S wherein W³ is —CH₂—.

Embodiment 26S

A compound of Formula 1S or any one of Embodiments 15 through 25S wherein G is G-2, G-3, G-9, G-15, G-18, G-19 or G-20 (as depicted in Embodiment 79).

Embodiment 27S

A compound of Embodiment 26S wherein when R¹ is G, then G is G-19 or G-20.

Embodiment 28S

A compound of Embodiment 27S wherein when R¹ is G, then G is G-19.

Embodiment 29S

A compound of Embodiment 28S wherein when R¹ is G, then G is G-20.

Embodiment 30S

A compound of Embodiment 26S wherein when R² is G, then G is G-2, G-3 or G-15.

Embodiment 31S

A compound of Embodiment 30R wherein when R² is G, then G is G-2.

Embodiment 32S

A compound of Embodiment 31R wherein when R² is G, then G is G-3.

Embodiment 33S

A compound of Formula 1R or any one of Embodiments 1R through 32R wherein each R²¹ is independently halogen, nitro, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy or C₁-C₆ alkylthio.

Embodiment 34S

A compound of Embodiment 33R wherein each R²¹ is independently fluorine, chlorine, bromine, CH₃, CF₃, OCH₃, OCF₃ or SCH₃.

Embodiment 35S

A compound of Formula 1R or any one of Embodiments 1R through 32R wherein each R²² is independently C₁-C₆ alkyl or C₁-C₆ haloalkyl.

Embodiment 36S

A compound of Embodiment 58Q wherein each R²² is independently CH₃ or CH₂CF₃.

Embodiment 37S

A compound of Formula 1S or any on of Embodiments 1S through 36S wherein when R²³ is an optionally substituted carbon moiety, R²³ is C₁-C₁₆ alkyl; or phenyl or benzyl optionally substituted with halogen, nitro, cyano or hydroxy on ring members.

Embodiment 38S

A compound of Embodiment 37S wherein when R²³ is an optionally substituted carbon moiety, R²³ is C₁-C₁₀ alkyl; or phenyl or benzyl optionally substituted with halogen or nitro on ring members.

Embodiment 39S

A compound of Embodiment 38S wherein when R²³ is an optionally substituted carbon moiety, R²³ is C₁-C₆ alkyl; or benzyl optionally substituted with halogen or nitro on ring members.

Embodiment 40S

A compound of Embodiment 39S wherein when R²³ is an optionally substituted carbon moiety, R²³ is C₁-C₆ alkyl; or unsubstituted benzyl.

Embodiment 41S

A compound of Embodiment 40S wherein when R²³ is an optionally substituted carbon moiety, R²³ is C₁-C₆ alkyl.

Embodiment 42S

A compound of Embodiment 41S wherein when R²³ is an optionally substituted carbon moiety, R²³ is unsubstituted benzyl.

Embodiment 43S

A compound of Embodiment 42S wherein when R²³ is an optionally substituted carbon moiety, R²³ is ethyl, n-propyl, n-butyl or i-propyl.

Embodiment 44S

A compound of Embodiment 43S wherein when R²³ is an optionally substituted carbon moiety, R²³ is ethyl, n-propyl or i-propyl.

Embodiment 45S

A compound of Embodiment 44S wherein when R²³ is an optionally substituted carbon moiety, R²³ is ethyl.

Embodiments of the present invention as described in the Summary of the Invention also include (where Formula 1P as used in the following Embodiments includes N-oxides and salts thereof):

Embodiment P1

A compound of Formula 1P wherein X is N.

Embodiment P2

A compound of Formula 1P wherein X is CH.

Embodiment P3

A compound of Formula 1P or any one of Embodiments P1 through P2 wherein Y is C(O).

Embodiment P4

A compound of Formula 1P or Embodiment P2 wherein Y is S(O)₂.

Embodiment P5

A compound of Formula 1P or any one of Embodiments P1 through P4 wherein A is A-1, A-3, A-4, A-5 or A-6.

Embodiment P6

A compound of Embodiment P5 wherein A is A-1, A-3, A-5 or A-6.

Embodiment P7

A compound of Embodiment P6 wherein A is A-3 or A-5.

Embodiment P8

A compound of Embodiment P7 wherein A is A-3.

Embodiment P9

A compound of Embodiment P6 wherein A is A-1 or A-6.

Embodiment P10

A compound of Embodiment P9 wherein A is A-1.

Embodiment P11

A compound of Formula 1P or any one of Embodiments P1 through P9 wherein A is other than A-1.

Embodiment P12

A compound of Formula 1P or any one of Embodiments P1 through P11 wherein B¹ is C-1.

Embodiment P13

A compound of Formula 1P or any one of Embodiments P1 through P11 wherein B¹ is C-2.

Embodiment P14

A compound of Formula 1P or any one of Embodiments P1 through P13 wherein B² is C-3.

Embodiment P15

A compound of Formula 1P or any one of Embodiments P1 through P13 wherein B² is C-4.

Embodiment P16

A compound of Formula 1P or any one of Embodiments P1 through P13 wherein B² is C-6

Embodiment P17

A compound of Formula 1P or any one of Embodiments P1 through P13 wherein B² is C-7.

Embodiment P18

A compound of Formula 1P or any one of Embodiments P1 through P17 wherein B³ is C-1.

Embodiment P19

A compound of Formula 1P or any one of Embodiments P1 through P17 wherein B³ is C-2.

Embodiment P20

A compound of Formula 1P or any one of Embodiments P1 through P19 wherein R¹ is phenyl, phenylsulfonyl, —W¹(phenyl), —W¹(S-phenyl), —W¹(SO₂-phenyl), —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each optionally substituted on ring members with up to five substituents selected from R²¹; or -G or —W²G; or cyano, hydroxy, amino, —C(═O)OH, —C(═O)NHCN, —C(═O)NHOH, —SO₂NH₂, —SO₂NHCN, —SO₂NHOH, —NHCHO, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈ alkylsulfonylalkyl, C₂-C₈ alkylaminoalkyl, C₃-C₁₀ dialkylaminoalkyl, C₂-C₈ haloalkylaminoalkyl, C₄-C₁₀ cycloalkylaminoalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈ alkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₅-C₁₂ cycloalkylalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₂-C₅ cyanoalkyl, C₁-C₆ hydroxyalkyl, C₄-C₁₀ cycloalkenylalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈ alkoxyhaloalkyl, C₂-C₈ haloalkoxyhaloalkyl, C₄-C₁₀ halocycloalkoxyalkyl, C₄-C₁₀ cycloalkenyloxyalkyl, C₄-C₁₀ halocycloalkenyloxyalkyl, C₃-C₁₀ dialkoxyalkyl, C₃-C₁₀ alkoxyalkylcarbonyl, C₃-C₁₀ alkoxycarbonylalkyl or C₂-C₈ haloalkoxycarbonyl.

Embodiment P21

A compound of Embodiment P20 wherein R¹ is phenyl, —W¹(phenyl), —W¹(S-phenyl), —W¹(SO₂-phenyl), —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each optionally substituted on ring members with up to five substituents selected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈ cycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl or C₂-C₈ alkylsulfonylalkyl.

Embodiment P22

A compound of Embodiment P21 wherein R¹ is phenyl or —W¹(phenyl), each optionally substituted on ring members with up to two substituents selected from R²¹; or C₁-C₆ alkyl or C₂-C₆ alkenyl.

Embodiment P23

A compound of Embodiment P22 wherein R¹ is phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 4-methylphenyl, 2-methylphenyl, 4-methoxyphenyl, 2,3-dimethylphenyl, CH₂(phenyl), CH₃ or CH₂CH₃.

Embodiment P24

A compound of Embodiment P23 wherein R¹ is phenyl.

Embodiment P25

A compound of Formula 1P or any one of Embodiments P1 through P22 wherein W¹ is C₁-C₆ alkylene.

Embodiment P26

A compound of Embodiment P25 wherein W¹ is —CH₂—.

Embodiment P27

A compound of Formula 1P or any one of Embodiments P1 through P21 or P25 or P26 wherein W² is —CH₂—.

Embodiment P28

A compound of Formula 1P or any one of Embodiments P1 through P27 wherein R² is phenyl or —W³(phenyl), each optionally substituted on ring members with up to five substituents selected from R²¹; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀ cycloalkoxyalkyl, C₄-C₁₀ cycloalkoxylalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈ alkylsulfonylalkyl, C₂-C₈ alkylcarbonyl, C₄-C₁₀ cycloalkenylalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈ alkoxyhaloalkyl, C₂-C₈ haloalkoxyhaloalkyl, C₄-C₁₀ halocycloalkoxyalkyl, C₄-C₁₀ cycloalkenyloxyalkyl, C₄-C₁₀ halocycloalkenyloxyalkyl, C₃-C₁₀ dialkoxyalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy, C₂-C₆ alkynyloxy, C₃-C₆ haloalkynyloxy, C₂-C₈ alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy, C₂-C₈ haloalkylcarbonyloxy, C₄-C₁₀ cycloalkylcarbonyloxy, C₃-C₁₀ alkylcarbonylalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₃-C₈ trialkylsilyl, C₃-C₈ cycloalkenyloxy, C₃-C₈ halocycloalkenyloxy, C₂-C₈ haloalkoxyalkoxy, C₂-C₈ alkoxyhaloalkoxy, C₂-C₈ haloalkoxyhaloalkoxy, C₃-C₁₀ alkoxycarbonylalkoxy, C₂-C₈ alkyl(thiocarbonyl)oxy, C₃-C₈ cycloalkylsulfinyl or C₃-C₁₀ halotrialkylsilyl.

Embodiment P29

A compound of Embodiment P28 wherein R² is phenyl or —W³(phenyl), each optionally substituted on ring members with up to two substituents selected from R²¹; or C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl, C₁-C₆ alkoxy, C₁-C₆ alkylthio or C₁-C₆ alkylsulfonyl.

Embodiment P30

A compound of Embodiment P29 wherein R² is phenyl or CH₂(phenyl), each optionally substituted on ring members with up to two substituents selected from R²¹; or C₁-C₆ alkyl, C₃-C₈ cycloalkyl or C₁-C₆ alkylthio.

Embodiment P31

A compound of Embodiment P30 wherein R² is phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, CH₂CH₃, cyclopropyl or SCH₃.

Embodiment P32

A compound of Formula 1P or any one of Embodiments P1 through P29 wherein W³ is C₁-C₆ alkylene.

Embodiment P33

A compound of Embodiment P32 wherein W³ is —CH₂—.

Embodiment P34

A compound of Formula 1P or any one of Embodiments P1 through P27 or P32 or P33 wherein W⁴ is —CH₂—.

Embodiment P35

A compound of Formula 1P or any one of Embodiments P1 through P34 wherein R³ is hydroxy, C₂-C₈ alkylcarbonyloxy, C₂-C₈ haloalkylcarbonyloxy, C₄-C₁₀ cycloalkylcarbonyloxy or C₃-C₁₀ alkylcarbonylalkoxy; or benzyloxy, phenyloxy, benzylcarbonyloxy, phenylcarbonyloxy, phenylsulfonyloxy or benzylsulfonyloxy, each optionally substituted on ring members with up to two substituents selected from R²¹.

Embodiment P36

A compound of Embodiment P35 wherein R³ is hydroxy or —O⁻M⁺; or phenylsulfonyloxy optionally substituted with up to two substituents selected from R²¹.

Embodiment P37

A compound of Embodiment P36 wherein R³ is hydroxy; or phenylsulfonyloxy substituted with CH₃ at the 4-position.

Embodiment P38

A compound of Formula 1P or any one of Embodiments P1 through P36 wherein M⁺ is a sodium or potassium metal cation.

Embodiment P39

A compound of Formula 1P or any of Embodiments P1 through P7 and P12 through P38 wherein R⁴, R⁵, R⁶ and R⁷ are each independently H, or C₁-C₆ alkyl.

Embodiment P40

A compound of Formula 1P or any one of Embodiments P1 through P7 and 12 through 39 wherein R⁸ is C₁-C₆ alkyl or C₃-C₈ cycloalkyl.

Embodiment P41

A compound of Embodiment P40 wherein R⁸ is CH₃, CH₂CH₃ or cyclopropyl.

Embodiment P42

A compound of Formula 1P or any one of Embodiments P1 through P9 and 12 through 41 wherein R⁹ is C₁-C₆ alkyl.

Embodiment P43

A compound of Embodiment P42 wherein R⁹ is CH₂CH₃.

Embodiment P44

A compound of Formula 1P or any one of Embodiments P1 through P9 and 12 through 41 wherein R¹⁰ is H, halogen or C₁-C₆ alkyl.

Embodiment P45

A compound of Embodiment P44 wherein R¹⁰ is H or CH₃.

Embodiment P46

A compound of Formula 1P or any one of Embodiments P1 through P8, P10, and P12 through P45 wherein R¹¹ is H or C₁-C₆ alkyl.

Embodiment P47

A compound of Embodiment P46 wherein R¹¹ is H.

Embodiment P48

A compound of Formula 1P or any one of Embodiments P1 through P8, P10, and P12 through P47 wherein R¹² is H, halogen, cyano, hydroxy, amino or C₁-C₆ alkyl.

Embodiment P49

A compound of Embodiment P48 wherein R¹² is H, halogen, cyano, C₁-C₆ alkyl or C₃-C₈ cycloalkyl.

Embodiment P50

A compound of Embodiment P49 wherein R¹² is CH₃, CH₂CH₃ or cyclopropyl.

Embodiment P51

A compound of Formula 1P or any one of Embodiments P1 through P6 and P12 through P50 wherein R¹³ is H, halogen, cyano or nitro.

Embodiment P52

A compound of Embodiment P51 wherein R¹³ is cyano or nitro.

Embodiment P53

A compound of Formula 1P or any one of Embodiments P1 through P52 wherein when instances of R¹⁴ and R¹⁸ are taken alone (i.e. R¹⁴ and R¹⁸ are not taken together as alkylene or alkenylene), then independently said instances of R¹⁴ and R¹⁸ are H or C₁-C₆ alkyl.

Embodiment P53a

A compound of Embodiment P53 wherein when instances of R¹⁴ and R¹⁸ are taken alone, then independently said instances of R¹⁴ and R¹⁸ are H or CH₃.

Embodiment P53b

A compound of Embodiment P53a wherein when instances of R¹⁴ and R¹⁸ are taken alone, then independently said instances of R¹⁴ and R¹⁸ are H.

Embodiment P53c

A compound of Formula 1P or any one of Embodiments P1 through P53b wherein when instances of R¹⁴ and R¹⁸ are taken together, then said instances of R¹⁴ and R¹⁸ are taken together as —CH₂CH₂CH₂— or —CH═CH—CH₂—.

Embodiment P53d

A compound of Formula 1P or any one of Embodiments P1 through P53b wherein all instances of R¹⁴ and R¹⁸ are taken alone.

Embodiment P54

A compound of Formula 1P or any one of Embodiments P1 through P53d wherein independently each R¹⁵ and R¹⁹ is H or C₁-C₆ alkyl.

Embodiment P54a

A compound of Embodiment P54 wherein independently each R¹⁵ and R¹⁹ is H or CH₃.

Embodiment P55

A compound of Embodiment P54a wherein independently each R¹⁵ and R¹⁹ is H.

Embodiment P56

A compound of Formula 1P or any one of Embodiments P1 through P55 wherein R²⁰ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl or C₃-C₈ cycloalkyl.

Embodiment P57

A compound of Embodiment P56 wherein R²⁰ is H or CH₃.

Embodiment P58

A compound of Formula 1P or any one of Embodiments P1 through P57 wherein T is —CH₂CH₂— or —CH═CH—.

Embodiment P59

A compound of Formula 1P or any one of Embodiments P1 through P58 wherein each G is independently a 5- or 6-membered heterocyclic ring optionally substituted with up to five substituents selected from R²¹ on carbon ring members and R²² on nitrogen ring members.

Embodiment P60

A compound of Embodiment P59 wherein G is selected from

-   -   r is 0, 1, 2 or 3.

Embodiment P61

A compound of Embodiment P60 wherein G is G-13, G-14, G-15, G-16 or G-17.

Embodiment P62

A compound of Formula 1P or any one of Embodiments P1 through P61 wherein each R²¹ is independently halogen, cyano, hydroxy, nitro, —CHO, —SH, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈ alkoxyhaloalkyl, C₂-C₅ cyanoalkyl, C₁-C₆ hydroxyalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy, C₂-C₈ alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl or C₃-C₈ cycloalkylsulfonyl.

Embodiment P63

A compound of Embodiment P62 wherein each R²¹ is independently halogen, nitro, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy or C₁-C₆ alkylthio.

Embodiment P64

A compound of Embodiment P61 wherein each R²¹ is independently fluorine, chlorine, CH₃, CF₃, OCH₃, OCF₃ or SCH₃.

Embodiment P65

A compound of Formula 1P or any one of Embodiments P1 through P64 wherein each R²² is independently C₁-C₆ alkyl or C₁-C₆ haloalkyl.

Embodiment P66

A compound of Embodiment P1 through 65 wherein each R²² is independently CH₃ or CH₂CF₃.

This invention also includes a herbicidal mixture of (a) a compound of Formula 1P and (b) an active ingredient selected from photosystem II inhibitors.

Embodiment P67

A herbicidal mixture comprising (a) a compound of Formula 1P and (b) an additional herbicidal ingredient selected from photosystem II inhibitors.

Embodiment P68

A herbicidal mixture of Embodiment P67 comprising (a) a compound of Formula 1P and (b) an additional herbicidal compound selected from the group consisting of ametryn, amicarbazone, atrazine, bentazon, bromacil, bromoxynil, chlorotoluron, diuron, hexazinone, isoproturon, metribuzin, pyridate, simazine and terbutryn.

Embodiment P69

A herbicidal mixture of Embodiment P68 comprising (a) a compound of Formula 1P; and (b) bromoxynil.

Embodiments of this invention, including Embodiments P1-P69 above as well as any other embodiments described herein, can be combined in any manner, and the descriptions of variables in the embodiments pertain not only to the compounds of Formula 1P but also to the starting compounds and intermediate compounds useful for preparing the compounds of Formula 1P. In addition, embodiments of this invention, including Embodiments 1-66 above as well as any other embodiments described herein, and any combination thereof, pertain to the compositions and methods of the present invention.

Combinations of Embodiments 1-66 are illustrated by:

Embodiment PA

A compound of Formula 1P wherein

-   -   Y is C(O);     -   A is A-1, A-3, A-5 or A-6;     -   R¹ is phenyl, phenylsulfonyl, —W¹(phenyl), —W¹(S-phenyl),         —W¹(SO₂-phenyl), —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each         optionally substituted on ring members with up to five         substituents selected from R²¹; or -G or —W²G; or cyano,         hydroxy, amino, —C(═O)OH, —C(═O)NHCN, —C(═O)NHOH, —SO₂NH₂,         —SO₂NHCN, —SO₂NHOH, —NHCHO, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆         alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl,         C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀ alkylcycloalkyl,         C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl, C₄-C₁₀         halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈         cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀         cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈         alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈         alkylsulfonylalkyl, C₂-C₈ alkylaminoalkyl, C₃-C₁₀         dialkylaminoalkyl, C₂-C₈ haloalkylaminoalkyl, C₄-C₁₀         cycloalkylaminoalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈         haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈         alkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₅-C₁₂         cycloalkylalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀         dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₂-C₅         cyanoalkyl, C₁-C₆ hydroxyalkyl, C₄-C₁₀ cycloalkenylalkyl, C₂-C₈         haloalkoxyalkyl, C₂-C₈ alkoxyhaloalkyl, C₂-C₈         haloalkoxyhaloalkyl, C₄-C₁₀ halocycloalkoxyalkyl, C₄-C₁₀         cycloalkenyloxyalkyl, C₄-C₁₀ halocycloalkenyloxyalkyl, C₃-C₁₀         dialkoxyalkyl, C₃-C₁₀ alkoxyalkylcarbonyl, C₃-C₁₀         alkoxycarbonylalkyl or C₂-C₈ haloalkoxycarbonyl;     -   W¹ is C₁-C₆ alkylene     -   W² is —CH₂—;     -   R² is phenyl or —W³(phenyl), each optionally substituted on ring         members with up to five substituents selected from R²¹; or C₁-C₆         alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆         haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈         halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl,         C₆-C₁₄ cycloalkylcycloalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂         alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈         halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀ cycloalkoxyalkyl,         C₄-C₁₀ cycloalkoxylalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈         alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈         alkylsulfonylalkyl, C₂-C₈ alkylcarbonyl, C₄-C₁₀         cycloalkenylalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈ alkoxyhaloalkyl,         C₂-C₈ haloalkoxyhaloalkyl, C₄-C₁₀ halocycloalkoxyalkyl, C₄-C₁₀         cycloalkenyloxyalkyl, C₄-C₁₀ halocycloalkenyloxyalkyl, C₃-C₁₀         dialkoxyalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₈         cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀ cycloalkylalkoxy,         C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy, C₂-C₆ alkynyloxy, C₃-C₆         haloalkynyloxy, C₂-C₈ alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy,         C₂-C₈ haloalkylcarbonyloxy, C₄-C₁₀ cycloalkylcarbonyloxy, C₃-C₁₀         alkylcarbonylalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₃-C₈         cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl,         C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₃-C₈         cycloalkylsulfonyl, C₃-C₈ trialkylsilyl, C₃-C₈ cycloalkenyloxy,         C₃-C₈ halocycloalkenyloxy, C₂-C₈ haloalkoxyalkoxy, C₂-C₈         alkoxyhaloalkoxy, C₂-C₈ haloalkoxyhaloalkoxy, C₃-C₁₀         alkoxycarbonylalkoxy, C₂-C₈ alkyl(thiocarbonyl)oxy, C₃-C₈         cycloalkylsulfinyl or C₃-C₁₀ halotrialkylsilyl;     -   W³ is C₁-C₆ alkylene;     -   W⁴ is —CH₂—;     -   R³ is hydroxy, —O⁻M⁺, C₂-C₈ alkylcarbonyloxy, C₂-C₈         haloalkylcarbonyloxy, C₄-C₁₀ cycloalkylcarbonyloxy or C₃-C₁₀         alkylcarbonylalkoxy; or benzyloxy, phenyloxy, benzylcarbonyloxy,         phenylcarbonyloxy, phenylsulfonyloxy or benzylsulfonyloxy, each         optionally substituted on ring members with up to two         substituents selected from R²¹;     -   M⁺ is a sodium or potassium metal cation;     -   R⁹ is C₁-C₆ alkyl;     -   R¹⁰ is H, halogen or C₁-C₆ alkyl;     -   R¹¹ is H or C₁-C₆ alkyl;     -   R¹² is H, halogen, cyano, hydroxy, amino or C₁-C₆ alkyl;     -   R¹³ is cyano or nitro;     -   each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is independently H or CH₃; or     -   a pair of R¹⁴ and R¹⁸ is taken together as —CH₂CH₂CH₂— or         —CH═CH—CH₂—;     -   R²⁰ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl or C₃-C₈ cycloalkyl;     -   T is —CH₂CH₂— or —CH═CH—;     -   each G is selected from G-1 through G-23 (as depicted in         Embodiment 79);     -   r is 0, 1, 2 or 3;     -   each R²¹ is independently halogen, cyano, hydroxy, nitro, —CHO,         —SH, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl,         C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈         halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl,         C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl,         C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈         alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈ alkoxyhaloalkyl,         C₂-C₅ cyanoalkyl, C₁-C₆ hydroxyalkyl, C₁-C₆ alkoxy, C₁-C₆         haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀         cycloalkylalkoxy, C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy, C₂-C₈         alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy, C₁-C₆ alkylthio, C₁-C₆         haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆         haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl         or C₃-C₈ cycloalkylsulfonyl; and     -   R²² is independently C₁-C₆ alkyl or C₁-C₆ haloalkyl.

Embodiment PB

A compound of Embodiment PA wherein

-   -   X is CH;     -   A is A-3 or A-5;     -   B² is C-3;     -   R¹ is phenyl, —W¹(phenyl), —W¹(S-phenyl), —W¹(SO₂-phenyl),         —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each optionally         substituted on ring members with up to five substituents         selected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl,         C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈         cycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl,         C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl,         C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl or C₂-C₈         alkylsulfonylalkyl;     -   R² is phenyl or —W³(phenyl), each optionally substituted on ring         members with up to two substituents selected from R²¹; or C₁-C₆         alkyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl, C₁-C₆ alkoxy, C₁-C₆         alkylthio or C₁-C₆ alkylsulfonyl;     -   R³ is hydroxy or —O⁻M⁺; or phenylsulfonyloxy optionally         substituted on ring members with up to two substituents selected         from R²¹;     -   R⁹ is CH₂CH₃;     -   R¹⁰ is H or CH₃;     -   W¹ is —CH₂—;     -   W³ is —CH₂—;     -   G is G-13, G-14, G-15, G-16 or G-17; and     -   each R²¹ is independently halogen, nitro, C₁-C₆ alkyl, C₁-C₆         haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy or C₁-C₆ alkylthio.

Embodiment PC

A compound of Embodiment PA wherein:

-   -   X is CH;     -   A is A-1 or A-6;     -   B¹ is C-1, B² is C-3 and B³ is C-1;     -   R¹ is phenyl, —W¹(phenyl), —W¹(S-phenyl), —W¹(SO₂-phenyl),         —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each optionally         substituted on ring members with up to five substituents         selected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl,         C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈         cycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl,         C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl,         C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl or C₂-C₈         alkylsulfonylalkyl;     -   R² is phenyl or —W³(phenyl), each optionally substituted on ring         members with up to two substituents selected from R²¹; or C₁-C₆         alkyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl, C₁-C₆ alkoxy, C₁-C₆         alkylthio or C₁-C₆ alkylsulfonyl;     -   R³ is hydroxy or —O⁻M⁺; or phenylsulfonyloxy optionally         substituted on ring members with up to two substituents selected         from R²¹;     -   R¹¹ is H;     -   each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is independently H or CH₃;     -   R¹² is H, halogen, cyano, C₁-C₆ alkyl or C₃-C₈ cycloalkyl;     -   W¹ is —CH₂—;     -   W³ is —CH₂—;     -   G is G-13, G-14, G-15, G-16 or G-17; and     -   each R²¹ is independently halogen, nitro, C₁-C₆ alkyl, C₁-C₆         haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy or C₁-C₆ alkylthio.

Embodiment PD

A compound of Embodiment PC wherein:

-   -   A is A-1;     -   R¹ is phenyl or —W¹(phenyl) each optionally substituted on ring         members with up to two substituents selected from R²¹; or C₁-C₆         alkyl or C₂-C₆ alkenyl;     -   R² is phenyl or CH₂(phenyl), each optionally substituted on ring         members with up to two substituents selected from R²¹; or C₁-C₆         alkyl, C₃-C₈ cycloalkyl or C₁-C₆ alkylthio;     -   R³ is hydroxy; or phenylsulfonyloxy substituted with CH₃ at the         4-position; and each R²¹ is independently fluorine, chlorine,         CH₃, CF₃, OCH₃, OCF₃ or SCH₃.

Embodiment PE

A compound of Embodiment PD wherein:

-   -   R¹ is phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl,         2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 4-methylphenyl,         2-methylphenyl, 4-methoxyphenyl, 2,3-dimethylphenyl,         CH₂(phenyl), CH₃ or CH₂CH₃;     -   R² is phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl,         CH₂CH₃, c-Pr or SCH₃.

Specific embodiments include the compound of Formula 1P which is:

-   5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2,3-diphenyl-4(3H)-pyrimidinone.

This invention also relates to a method for controlling undesired vegetation comprising applying to the locus of the vegetation a herbicidally effective amount of a compound of the invention (e.g., as a composition described herein). Of note as embodiments relating to methods of use are those involving the compounds of embodiments described above.

This invention also includes herbicidal mixture comprising (a) a compound of Formula 1P and (b) an additional herbicidal ingredient selected from a photosystem II inhibitor. Also noteworthy as embodiments are herbicidal compositions of the present invention comprising the compounds of embodiments described above.

“Photosystem II inhibitors” (b1) are chemical compounds that bind to the D-1 protein at the Q_(B)-binding niche and thus block electron transport from Q_(A) to Q_(B) in the chloroplast thylakoid membranes. The electrons blocked from passing through photosystem II are transferred through a series of reactions to form toxic compounds that disrupt cell membranes and cause chloroplast swelling, membrane leakage, and ultimately cellular destruction. The Q_(B)-binding niche has three different binding sites: binding site A binds the triazines such as atrazine, triazinones such as hexazinone, and uracils such as bromacil, binding site B binds the phenylureas such as diuron, and binding site C binds benzothiadiazoles such as bentazon, nitriles such as bromoxynil and phenyl-pyridazines such as pyridate. Examples of photosystem II inhibitors include, but are not limited to ametryn, atrazine, cyanazine, desmetryne, dimethametryn, prometon, prometryne, propazine, simazine, simetryn, terbumeton, terbuthylazine, terbutryne, trietazine, hexazinone, metamitron, metribuzin, amicarbazone, bromacil, lenacil, terbacil, chloridazon, desmedipham, phenmedipham, chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, ethidimuron, fenuron, fluometuron, isoproturon, isouron, linuron, methabenzthiazuron, metobromuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron, propanil, pentanochlor, bromofenoxim, bromoxynil, ioxynil, bentazon, pyridate and pyridafol.

“AHAS inhibitors” (b2) are chemical compounds that inhibit acetohydroxy acid synthase (AHAS), also known as acetolactate synthase (ALS), and thus kill plants by inhibiting the production of the branched-chain aliphatic amino acids such as valine, leucine and isoleucine, which are required for DNA synthesis and cell growth. Examples of AHAS inhibitors include but are not limited to amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flupyrsulfuron-methyl (including sodium salt), foramsulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron-methyl (including sodium salt), mesosulfuron-methyl, metazosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, trifloxysulfuron (including sodium salt), triflusulfuron-methyl, tritosulfuron, imazapic, imazamethabenz-methyl, imazamox, imazapyr, imazaquin, imazethapyr, cloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam, bispyribac-sodium, pyribenzoxim, pyriftalid, pyrithiobac-sodium, pyriminobac-methyl, thiencarbazone, flucarbazone-sodium and propoxycarbazone-sodium.

“ACCase inhibitors” (b3) are chemical compounds that inhibit the acetyl-CoA carboxylase enzyme, which is responsible for catalyzing an early step in lipid and fatty acid synthesis in plants. Lipids are essential components of cell membranes, and without them, new cells cannot be produced. The inhibition of acetyl CoA carboxylase and the subsequent lack of lipid production leads to losses in cell membrane integrity, especially in regions of active growth such as meristems. Eventually shoot and rhizome growth ceases, and shoot meristems and rhizome buds begin to die back. Examples of ACCase inhibitors include but are not limited to clodinafop, cyhalofop, diclofop, fenoxaprop, fluazifop, haloxyfop, propaquizafop, quizalofop, alloxydim, butroxydim, clethodim, cycloxydim, pinoxaden, profoxydim, sethoxydim, tepraloxydim and tralkoxydim, including resolved forms such as fenoxaprop-P, fluazifop-P, haloxyfop-P and quizalofop-P and ester forms such as clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl and fenoxaprop-P-ethyl.

Auxin is a plant hormone that regulates growth in many plant tissues. “Auxin mimics” (b4) are chemical compounds mimicking the plant growth hormone auxin, thus causing uncontrolled and disorganized growth leading to plant death in susceptible species. Examples of auxin mimics include but are not limited to aminocyclopyrachlor, aminopyralid benazolin-ethyl, chloramben, clomeprop, clopyralid, dicamba, 2,4-D, 2,4-DB, dichlorprop, fluroxypyr, mecoprop, MCPA, MCPB, 2,3,6-TBA, picloram, triclopyr, quinclorac, quinmerac.

“EPSP (5-enol-pyruvylshikimate-3-phosphate) synthase inhibitors” (b5) are chemical compounds that inhibit the enzyme, 5-enol-pyruvylshikimate-3-phosphate synthase, which is involved in the synthesis of aromatic amino acids such as tyrosine, tryptophan and phenylalanine. EPSP inhibitor herbicides are readily absorbed through plant foliage and translocated in the phloem to the growing points. Glyphosate is a relatively nonselective postemergence herbicide that belongs to this group. Glyphosate includes esters and salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium) and trimesium (alternatively named sulfosate).

One or more of the following methods and variations as described in Schemes 1-18 can be used to prepare the compounds of Formula 1. The definitions of A, B¹, B², B³, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹² and R¹³ in the compounds of Formulae 1-34 below are as defined above in the Summary of the Invention unless otherwise noted. Compounds of Formulae 1a-1h are various subsets of the compounds of Formula 1, and all substituents for Formulae 1a-1h are as defined above for Formula 1.

Compounds of Formula 1a, 1b or 1c (where R³ is hydroxy) can be prepared via the two-step process shown in Schemes 1a, 1b and 1c respectively. Intermediate 4a, 4b or 4c can be prepared by reacting dione 2 with intermediate 3 where G is a nucleophilic reaction leaving group (e.g., G¹ is a halogen, alkoxycarbonyl, haloalkylcarbonyloxy, haloalkoxycarbonyloxy, pyridinyl or imidazoyl group). Reaction of intermediate 4a, 4b or 4c with the appropriate cyano compound (e.g., acetone cyanohydrin, potassium cyanide, sodium cyanide) in the presence of a base such as triethylamine or pyridine leads to a compound of Formula 1a, 1b or 1c. Alternatively a fluoride anion source such as potassium fluoride or cesium fluoride and optionally in the presence of a phase transfer catalyst (e.g. tetrabutyl ammonium bromide, etc.) can be used in this transformation. A solvent such as dimethylsulfoxide, N,N-dimethylformamide, acetonitrile or dichloromethane at ambient temperature to the reflux temperature of the solvent can lead to a compound of Formula 1a, 1b or 1c. (Formula 1a is Formula 1 wherein A is A-1; Formula 1b is Formula 1 wherein A is A-2; Formula 1c is Formula 1 wherein A is A-3.) Alternatively, compounds of Formula 1a, 1b or 1c can be prepared by Process 2 (in Schemes 1a, 1b and 1c respectively) by reacting dione 2a, 2b or 2c with intermediate 3 in the presence of a cyano compound or a fluoride anion source along with a base. For additional reaction conditions for this general coupling methodology, see Edmunds, A. in Modern Crop Protection Compounds; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.3 and references cited therein.

Compounds of Formula 1a, 1b or 1c can also be prepared as shown in Scheme 2, by reacting dione 2a, 2b or 2c with intermediate 3a in the presence of a base or Lewis acid. For reaction conditions for this general coupling methodology, see Edmunds, A. in Modern Crop Protection Compounds; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.3 and references cited therein.

As shown in Scheme 3, intermediate 4a, 4b or 4c can also be prepared by allowing dione 2a, 2b or 2c to react with acid 6 in the presence of a dehydrating condensation agent such as 2-chloro-1-pyridinium iodide (known as the Mukaiyama coupling agent), dicyclohexyl carbodiimide (DCC) or the like and optionally in the presence of a base. For additional reaction conditions for this general enol ester coupling methodology, see Edmunds, A. in Modern Crop Protection Compounds; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.3 and references cited therein.

Intermediate 4a, 4b or 4c can also be made by the palladium-catalyzed carbonylation reaction of a compound of Formula 7 in the presence of dione 2a, 2b or 2c (Scheme 4). For reaction conditions for this general enol ester forming methodology, see Edmunds, A. in Modern Crop Protection Compounds; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.3 and references cited therein.

Compounds of Formula 1a, 1b or 1c (where R³ is bonded through oxygen) are prepared by reacting compounds of Formula 1a, 1b or 1c with intermediate 8 where X is a nucleophilic reaction leaving group, also known as a nucleofuge in the presence of a base as shown in Scheme 5. Alternatively, compounds of Formula 1a, 1b and 1c (where R³ is bonded through nitrogen, sulfur or carbon) can be prepared using the appropriate halogenating agent followed by nucleophilic addition. For reaction conditions for this general functionalization method, see Edmunds, A. or Almisick A. V. in Modern Crop Protection Compounds; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.3 or Chapter 4.4, and references cited therein.

As shown in Scheme 6, compounds of Formula 1d (i.e. Formula 1 wherein A is A-4 and R³ is OH) can be prepared by the reaction of intermediate 9 with intermediate 3 in the presence of a Lewis base, for example n-butyllithium or lithium diisopropylamide in an appropriate solvent such as tetrahydrofuran or diethyl ether. For reaction conditions for this type of transformation, see JP 2003327580.

Compounds of Formula 1e (i.e. Formula 1 wherein A is A-5 and R³ is OH) can be prepared via a two-step process as shown in Scheme 7. Intermediate 12 can be prepared by reacting pyrazole 11 with intermediate 3 where G¹ is a nucleophilic reaction leaving group (i.e. G¹ is a halogen atom, alkoxycarbonyl, haloalkylcarbonyloxy, benzoyloxy, pyridinyl or imidazoyl group). Reaction of intermediate 12 with the appropriate cyano compound in the presence of a base leads to a compound of Formula 1e. Alternatively, a compound of Formula 1e can be prepared directly by reacting intermediate 11 with intermediate 3 (Process 2, Scheme 7) in the presence of a cyano compound or a fluoride anion source with a base. For reaction conditions for this general coupling methodology, see Almisick A. V. in Modern Crop Protection Compounds; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.4, and references cited therein.

Compounds of Formula 1f (i.e. Formula 1 wherein A is A-5) wherein R³ is bonded through oxygen can be prepared by reacting a compound of Formula 1e with intermediate 8 (where X is a nucleophilic reaction leaving group, also known as a nucleofuge) in the presence of a base as shown in Scheme 8. Alternatively compounds of Formula 1f wherein R³ is bonded through nitrogen, sulfur or carbon can be prepared using the appropriate halogenating agent followed by nucleophilic displacement. For reaction conditions for these general functionalization methods, see Almisick A. V. in Modern Crop Protection Compounds; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.4, and references cited therein.

Compounds of Formula 17 can be prepared by reacting intermediate 3 with a compound Formula 16 in an appropriate solvent in the presence of a base. Thereafter intermediate 17 can be rearranged into the compound of Formula 1g (i.e. Formula 1 wherein A is A-7) in the presence of a cyano compound and a base as shown in Scheme 9. For reaction conditions for this general coupling methodology, see Almisick A. V. in Modern Crop Protection Compounds; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.4, and references cited therein.

Compounds of Formula 19 can be prepared from corresponding compounds of Formula 1g wherein R¹³ is an alkoxycarbonyl in the presence of an acid such as hydrogen chloride, sulfuric or acetic acid and optionally in the presence of a solvent such as tetrahydrofuran, diethyl ether or dichloromethane as shown in Scheme 10. Intermediate 19 is then reacted with an orthoformate ester or N,N-dimethylformamide dimethylacetal (DMF-DMA) in the presence of an acid to obtain intermediate 20. Reaction of intermediate 20 with hydroxylamine hydrochloride salt in a solvent such as ethanol, acetonitrile, water or acetic acid provides isoxazole compounds of Formula 1h (i.e. Formula 1 wherein A is A-6 and R¹¹ is H). For reaction conditions for this general cyclization methodology, see Almisick A. V. in Modern Crop Protection Compounds; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.4, and references cited therein.

As illustrated in Scheme 11, sulfoxides and sulfones of Formula 1 wherein R² is a substituent bonded through a sulfoxide or sulfone radical can be prepared by oxidation of the compounds of Formula 1 wherein R² is a substituent bonded through a sulfide radical. In a typical procedure, an oxidizing agent in an amount from 1 to 4 equivalents depending on the oxidation state of the product desired is added to a solution of the compound of Formula 1 in a solvent. Useful oxidizing agents include Oxone® (potassium peroxymonosulfate), hydrogen peroxide, sodium periodate, peracetic acid and 3-chloroperbenzoic acid. The solvent is selected with regard to the oxidizing agent employed. Aqueous ethanol or aqueous acetone is preferably used with potassium peroxymonosulfate, and dichloromethane is generally preferable with 3-chloroperbenzoic acid. Useful reaction temperatures typically range from 0 to 90° C. Particular procedures useful for oxidizing sulfides to sulfoxides and sulfones are described by Brand et al., J. Agric. Food Chem. 1984, 32, 221-226 and references cited therein.

One skilled in the art will realize that acid chlorides of Formula 3d (i.e. Formula 3 wherein G¹ is Cl) are easily prepared from the acid of Formula 6 (Scheme 12) by numerous well-known methods. For example reacting the acid with a chlorinating reagent such as oxalyl chloride or thionyl chloride in a solvent such as dichloromethane or toluene and optionally in the presence of a catalytic amount of N,N-dimethylformamide can provide the corresponding acid chloride of Formula 3d.

Compounds of Formula 6 can be prepared from esters of Formula 23 by numerous well-known methods, for example standard saponification procedures using aqueous bases such as LiOH, NaOH or KOH in a solvent such methanol or ethanol as described in Scheme 13. Alternatively, a dealkylating agent such as lithium iodide or trimethylsilyl iodide can be used in the presence of a base in a solvent such as pyridine or ethyl acetate. Additional reaction procedures for deesterification can be found in PCT Patent Publication WO 2006/133242. Boron tribromide (BBr₃) can alternatively be used to prepare a compound of Formula 6 from a compound of Formula 23 in a solovent such as dichloromethane. Procedures using boron tribromide can be found in Bioorg. & Med. Chem. Lett. 2009, 19(16), 4733-4739.

Pyrimidinone esters of Formula 23a (i.e. Formula 23 whererin Alk is ethyl, X is CH and Y is C(O)) are prepared as illustrated in Scheme 14 by N-alkylation of pyridones of Formula 26 with agents such as alkyl halides in the presence of a base such as sodium hydride or potassium carbonate in a solvent such as N,N-dimethylformamide, tetrahydrofuran or diethyl ether.

Pyrimidinone esters of Formula 23a can be made by the method of Scheme 15. In this method an methylene malonate of Formula 28 is cyclized with an amidine salt of Formula 29 wherein X is a halogen or sulfonate counter ion in the presence of excess base such as sodium alkoxide or potassium carbonate in an appropriate solvent such as ethanol (generally at the reflux temperature of the solvent) to give the corresponding pyrimidinone of Formula 3f. Examples of this synthetic method are reported in PCT Patent Publication WO 2006/133242 or Tetrahedron 2001, 57, 2689.

Pyrimidinone esters of Formula 26 can be prepared by the method of Scheme 16. In this method, an ethylene malonate of Formula 28 is cyclized with an amidine salt Formula 29a wherein X is a halogen or sulfonate counter ion in the presence of excess base such as sodium alkoxide or potassium carbonate in an appropriate solvent such as methanol (generally at the reflux temperature of the solvent) to give the corresponding pyrimidinone of Formula 26. Examples of this synthetic procedure are reported in PCT Patent Publication WO 2006/133242, Tetrahedron 2001, 57, 2689.

Thiones of Formula 23b (i.e. Formula 23 wherein Alk is ethyl, X is CH and Y is S(O)₂) can be made by the method of Scheme 17. In this method amidines of Formula 29 is reacted with acetal 30 in the presence of a base such as triethylamine, pyridine or potassium carbonate to give the corresponding azabutadiene 31. Reacting this compound with the sulfonic acid chloride 32 as shown in Scheme 17 in the presence of a base such as triethylamine, pyridine or potassium carbonate in an appropriate solvent results in the corresponding compound of Formula 33. The corresponding thiones of formula 23b can be obtained by reacting the compound of Formula 33 with iodomethane and subsequent treatment with a base such as triethylamine. Examples of this synthetic methodology are reported in Synthesis 2000, 5, 695.

Triazines of Formula 23c (i.e. Formula 23 wherein Alk is ethyl, X is N and Y is C(O)) can be made by the method of Scheme 18. In this method a ketomalonate of Formula 34 is cyclized with a semicarbazide of Formula 29c wherein X is a halogen or sulfonate counter ion with or without the presence of excess base such as sodium alkoxide or potassium carbonate in an appropriate solvent such as ethanol or t-butanol (generally at the reflux temperature of the solvent) to the corresponding triazine of Formula 23c. Examples of this synthetic methodology are found in Eur. J. Med. Chem. 2008, 43(5), 1085, Bull. Soc. Chim. Fr. 1976, (11-12, Pt. 2), 1825 and J. Org. Chem. 1962, 27, 976.

It is recognized that some reagents and reaction conditions described above for preparing compounds of Formula 1 may not be compatible with certain functionalities present in the intermediates. In these instances, the incorporation of protection/deprotection sequences or functional group interconversions into the synthesis will aid in obtaining the desired products. The use and choice of the protecting groups will be apparent to one skilled in chemical synthesis (see, for example, Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art will recognize that, in some cases, after the introduction of a given reagent as it is depicted in any individual scheme, it may be necessary to perform additional routine synthetic steps not described in detail to complete the synthesis of compounds of Formula 1. One skilled in the art will also recognize that it may be necessary to perform a combination of the steps illustrated in the above schemes in an order other than that implied by the particular sequence presented to prepare the compounds of Formula 1.

One skilled in the art will also recognize that compounds of Formula 1 and the intermediates described herein can be subjected to various electrophilic, nucleophilic, radical, organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents.

Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following Examples are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever. Steps in the following Examples illustrate a procedure for each step in an overall synthetic transformation, and the starting material for each step may not have necessarily been prepared by a particular preparative run whose procedure is described in other Examples or Steps. Percentages are by weight except for chromatographic solvent mixtures or where otherwise indicated. Parts and percentages for chromatographic solvent mixtures are by volume unless otherwise indicated. ¹H NMR spectra are reported in ppm downfield from tetramethylsilane at 400 MHz unless otherwise noted; “s” means singlet, “m” means multiplet, “br s” means broad singlet, “d” means doublet, “t” means triplet, “dt” means doublet of triplets, “q” means quartet and “sep” means septet.

Example 1 Preparation of 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2,3-diphenyl-4(3H)-pyrimidinone (Compound 2) Step A: Preparation of N-phenylbenzenecarboximidamide sodium salt

To a stirred solution of sodium bis(trimethylsilyl)amide (1.0 M in tetrahydrofuran, 21.5 mL, 21.5 mmol) in tetrahydrofuran (10 mL) was added aniline (2.0 g, 21.5 mmol) and allowed to stir for 10 min at room temperature. Benzonitrile (2.21 g, 21.5 mmol) was added, and the reaction mixture was stirred for 1 h at room temperature. The solid that precipitated was filtered, washed with diethyl ether and dried under reduced pressure to afford the title product as an off-white solid (4.0 g), which was used without further purification in the next step.

Step B: Preparation of (A) 1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylic acid ethyl ester and (B) 1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylic acid

To a stirred solution of N-phenylbenzenecarboximidamide sodium salt (i.e. the product from Step A) (6.0 g, 27.5 mmol) in acetonitrile (30 mL) was added ammonium chloride (1.47 g, 27.5 mmol) followed by diethyl ethoxymethylenemalonate (5.94 g, 27.5 mmol). The reaction mixture was heated and stirred at reflux for 2 h. The reaction mixture was concentrated under reduced pressure to give a residue. Water (30 mL) was added to the residue, followed by a saturated solution of sodium bicarbonate (30 mL), and the mixture was extracted with ethyl acetate. The aqueous layer was separated and retained. The organic layer was dried (MgSO₄) and concentrated under reduced pressure. The resulting residue was purified by column chromatography eluting with 30% ethyl acetate in hexanes to afford the title product (A) as a white solid (2.80 g).

¹H NMR (CDCl₃) δ 8.81 (s, 1H), 7.11-7.33 (m, 10H), 4.41 (m, 2H), 1.39 (m, 3H).

The above retained aqueous layer was acidified with 1 N hydrochloric acid until the pH was 1-2, and the mixture was extracted with dichloromethane. The organic layer was dried (MgSO₄) and concentrated under reduced pressure to provide a solid, which was washed with diethyl ether and dried under reduced pressure to afford the title product (B) as a white solid (680 mg).

¹H NMR (DMSO-d₆) δ 13.03 (s, 1H), 8.79 (s, 1H), 7.22-7.36 (m, 10H).

Step B1: Preparation of 1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylic acid (alternate preparation to Step B, product (B))

To a stirred solution of 1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylic acid ethyl ester (i.e. Step B product (A)) (2.30 g, 7.18 mmol) in pyridine (15 mL) was added lithium iodide (2.46 g, 18.0 mmol). The reaction mixture was heated to reflux with stirring for 24 h. The reaction mixture was concentrated under reduced pressure. To the resulting residue was added water (10 mL) followed by 1 N hydrochloric acid until the pH was 7. The solution was filtered though Celite® diatomaceous filter aid. The filtrate was acidified with 1 N hydrochloric acid until the pH was 1, and the mixture was extracted with dichloromethane. The organic layer was dried (MgSO₄) and concentrated under reduced pressure to afford a solid, which was washed with diethyl ether and dried under reduced pressure to afford the title product as a white solid (1.40 g).

¹H NMR (DMSO-d₆) δ 13.03 (s, 1H), 8.79 (s, 1H), 7.22-7.36 (m, 10H).

Step C: Preparation of 3-oxo-1-cyclohexen-1-yl 1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylate

To a stirred solution of 1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylic acid (i.e. Step B product (B) or the product from Step B1) (1.40 g, 4.8 mmol) in dichloromethane (30 mL) was added oxalyl chloride (1.21 g, 9.61 mmol) at 0° C. followed by catalytic amount (2 drops) of N,N-dimethylformamide. The reaction mixture was allowed to warm to room temperature and stir for 1 h. Then the reaction mixture was concentrated under reduced pressure. To the resulting residue was added dichloromethane (30 mL), 1,3-cyclohexanedione (646 mg, 5.76 mmol), followed by triethylamine (976 mg, 9.60 mmol), and the reaction mixture was stirred at room temperature for 30 min. Saturated aqueous ammonium chloride solution was added, and the mixture was extracted with dichloromethane. The organic layer was dried (MgSO₄) and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 50% ethyl acetate in hexanes to afford the title product as a white solid (1.1 g).

¹H NMR (CDCl₃) δ 8.89 (s, 1H), 7.31-7.36 (m, 5H), 7.24-7.26 (m, 3H), 7.12-7.15 (m, 2H), 6.04 (m, 1H), 2.68 (m, 2H), 2.45 (m, 2H), 2.11 (m, 2H).

Step D: Preparation of 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2,3-diphenyl-4(3H)-pyrimidinone (Compound 2)

To a stirred solution of 3-oxo-1-cyclohexen-1-yl 1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylate (i.e. the product from Step C) (640 mg, 1.65 mmol) in acetonitrile (20 mL) was added triethylamine (401 mg, 3.97 mmol), followed by a catalytic amount of acetone cyanohydrin (3 drops). The reaction mixture was stirred for 24 h at room temperature and then concentrated under reduced pressure. To the resulting residue was added dichloromethane and 1 N hydrochloric acid. The organic layer was separated, and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried (MgSO₄) and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 100% ethyl acetate to afford the title product, a compound of the present invention, as a white solid (150 mg).

¹H NMR (CDCl₃) δ 8.24 (s, 1H), 7.12-7.34 (m, 10H), 2.70 (m, 2H), 2.48 (m, 2H), 2.03 (m, 2H).

Example 2 Preparation of 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-3-(phenylmethyl)-4(3H)-pyrimidinone (Compound 17) Step A: Preparation of N-(phenylmethyl)-benzenecarboximidamide

To a stirred solution of ethylbenzimidate hydrochloride (3.0 g, 16.2 mmol) in N,N-dimethylformamide (10 mL) was added triethylamine (1.60 g, 16.2 mmol). The reaction mixture was allowed to stir at room temperature for 1 h and then filtered to remove triethylamine salts, which were rinsed with N,N-dimethylformamide (5 mL). Benzylamine (1.23 g, 11.5 mmol) was added to the filtrate, and the mixture was heated to 65° C. for 24 h. To the cooled mixture was added water (80 mL) and ethyl acetate. The organic layer was washed with water and brine, then dried (MgSO₄) and concentrated under reduced pressure to afford the title product as a clear oil (2.80 g).

¹H NMR (CDCl₃) δ 7.61 (m, 2H), 7.26-4.43 (m, 8H), 4.57 (m, 2H), 4.37 (m, 1H), 1.42 (m, 1H).

Step B: Preparation of ethyl 1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylate

To a stirred solution of N-(phenylmethyl)-benzenecarboximidamide (i.e. the product from Step A) (2.54 g, 12.1 mmol) in ethanol (15 mL) was added diethyl ethoxymethylenemalonate (2.61 g, 12.1 mmol), and the reaction mixture was heated to reflux for 24 h. The reaction mixture was then allowed to cool to room temperature and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 30% ethyl acetate in hexanes to afford the title product as a white solid (2.9 g).

¹H NMR (CDCl₃) δ 8.71 (s, 1H), 7.51 (m, 1H), 7.42 (m, 2H), 7.33 (m, 2H), 7.23 (m, 3H), 6.93 (m, 2H), 5.28 (s, 2H), 4.42 (m, 2H), 1.40 (m, 3H).

Step C: Preparation of 1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylic acid

To a stirred solution of ethyl 1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylate (i.e. the product from Step B) (2.9 g, 8.6 mmol) in pyridine (15 mL) was added lithium iodide (3.01 g, 21.7 mmol). The reaction mixture was heated to reflux for 4 h, cooled, and then stirred at room temperature for 72 h. The reaction mixture was concentrated under reduced pressure. To the resulting residue was added water (10 mL), followed by 1 N hydrochloric acid until the pH was 7. The solution was filtered through Celite® diatomaceous filter aid, and the filtrate was acidified with 1 N hydrochloric acid until the pH was 1. The mixture was extracted with dichloromethane, and the organic layer was dried (MgSO₄) and concentrated under reduced pressure to afford a solid, which was washed with diethyl ether and dried under reduced pressure to afford the title product as a white solid (2.2 g).

Step D: Preparation of 3-oxo-1-cyclohexen-1-yl 1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylate

To a stirred solution of 1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylic acid (i.e. the product from Step C) (1.00 g, 3.26 mmol) in dichloromethane (30 mL) at 0° C., was added oxalyl chloride (823 mg, 6.53 mmol) followed by a catalytic amount of N,N-dimethylformamide (2 drops). The reaction mixture was allowed to warm to room temperature and stir for 1 h. Then the reaction mixture was concentrated under reduced pressure. To the resulting residue was added dichloromethane (30 mL) and 1,3-cyclohexanedione (440 mg, 3.90 mmol), followed by triethylamine (990 mg, 9.80 mmol), and the reaction mixture was stirred at room temperature for 30 min Saturated aqueous ammonium chloride solution was added to the reaction mixture, which was then extracted with dichloromethane. The organic layer was dried (MgSO₄) and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 50% ethyl acetate in hexanes to afford the title product as a white solid (500 mg).

¹H NMR (CDCl₃) δ 8.81 (s, 1H), 7.55 (m, 1H), 7.45 (m, 2H), 7.37 (m, 2H), 7.25 (m, 3H), 6.95 (m, 2H), 6.03 (s, 1H), 5.30 (s, 2H), 2.69 (m, 2H), 2.46 (m, 2H), 2.12 (m, 2H).

Step E: Preparation of 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-3-(phenylmethyl)-4(3H)-pyrimidinone (Compound 17)

To a stirred solution of 3-oxo-1-cyclohexen-1-yl 1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylate (i.e. the product from Step D) (450 mg, 1.12 mmol) in acetonitrile (15 mL) was added triethylamine (272 mg, 2.69 mmol), followed by a catalytic amount (3 drops) of acetone cyanohydrin. The reaction mixture was stirred for 24 h at room temperature and then concentrated under reduced pressure. To the resulting residue were added dichloromethane and 1 N hydrochloric acid, and the aqueous layer was extracted with dichloromethane. The organic layer was dried (MgSO₄) and concentrated under reduced pressure. The residue was purified by column chromatography eluting with ethyl acetate to afford the title product, a compound of the present invention, as a white solid (160 mg).

¹H NMR (CDCl₃) δ 16.44 (br s, 1H), 8.17 (s, 1H), 7.47 (m, 1H), 7.37 (m, 2H), 7.21-7.30 (m, 5H), 6.95 (m, 2H), 5.20 (s, 2H), 2.72 (m, 2H), 2.51 (m, 2H), 2.06 (m, 2H).

Example 3 Preparation of 5-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)carbonyl]-2-phenyl-3-(phenylmethyl)-4(3H)-pyrimidinone (Compound 20) Step A: Preparation of 1-ethyl-1H-pyrazol-5-yl 1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylate

To a stirred solution of 1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylic acid (i.e. the product from Example 2, Step C) (1.20 g, 3.92 mmol) in dichloromethane (30 mL) was added oxalyl chloride (998 mg, 7.84 mmol) at 0° C. followed by a catalytic amount (4-drops) of N,N-dimethylformamide. The reaction mixture was allowed to warm to room temperature and stir for 1 h. The reaction mixture was then concentrated under reduced pressure. To the resulting residue was added dichloromethane (30 mL) and 5-hydroxy-1-ethyl-1H-pyrazole, (572 mg, 4.7 mmol), followed by triethylamine (1.18 g, 11.8 mmol), and the reaction mixture was stirred at room temperature for 30 min. Saturated aqueous ammonium chloride solution was added to the reaction mixture, which was then extracted with dichloromethane. The organic layer was dried (MgSO₄) and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 70% ethyl acetate in hexanes to afford the title product as a white solid (700 mg).

¹H NMR (CDCl₃) δ 8.90 (s, 1H), 7.56 (m, 1H), 7.46 (m, 3H), 7.38 (m, 2H), 7.26 (m, 3H), 6.95 (m, 2H), 6.29 (m, 1H), 5.34 (s, 2H), 4.19 (m, 2H), 1.45 (m, 3H).

Step B: Preparation of 5-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)carbonyl]-2-phenyl-3-(phenylmethyl)-4(3H)-pyrimidinone (Compound 20)

To a stirred solution of 1-ethyl-1H-pyrazol-5-yl 1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylate (i.e. the product from Step A) (650 mg, 1.62 mmol) in acetonitrile (15 mL) was added triethylamine (393 mg, 3.70 mmol), followed by a catalytic amount (5 drops) of acetone cyanohydrin. The reaction mixture was stirred for 24 h at room temperature and then concentrated under reduced pressure. To the residue were added dichloromethane and 1 N hydrochloric acid, and the aqueous layer was extracted with dichloromethane. The organic layer was dried (MgSO₄) and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 10% methanol in ethyl acetate to afford the title product, a compound of the present invention, as a white solid (150 mg).

¹H NMR (CDCl₃) δ 8.56 (s, 1H), 7.86 (s, 1H), 7.53 (m, 1H), 7.39-7.46 (m, 4H), 7.24 (m, 3H), 6.97 (m, 2H), 5.33 (s, 2H), 4.04 (m, 2H), 1.42 (m, 3H).

Example 4 Step A: Preparation of 5-[[1-ethyl-5-[[(4-methylphenyl)sulfonyl]oxy]-1H-pyrazol-4-yl]carbonyl]-2-phenyl-3-(phenylmethyl)-4(3H)-pyrimidinone (Compound 21)

To a stirred solution of 5-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)carbonyl]-2-phenyl-3-(phenylmethyl)-4(3H)-pyrimidinone (i.e. the product from Example 3, Step B) (300 mg, 0.75 mmol) in acetonitrile (10 mL) was added triethylamine (116 mg, 1.12 mmol), followed by p-toluenesulfonyl chloride (171 mg, 0.90 mmol), and the reaction mixture was stirred at room temperature for 72 h. Saturated aqueous ammonium chloride solution was added to the mixture, and the aqueous layer was extracted with dichloromethane. The organic layer was dried (MgSO₄) and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 50% ethyl acetate in hexanes to afford the title product, a compound of the present invention, as a white solid (160 mg).

¹H NMR (CDCl₃) δ 8.07 (s, 1H), 7.84 (s, 1H), 7.74 (m, 2H), 7.44 (m, 2H), 7.25-7.35 (m, 8H), 6.95 (m, 2H), 5.23 (s, 2H), 4.00 (m, 2H), 2.41 (s, 3H), 1.42 (m, 3H).

Example 5 Preparation of 3-(3-fluoro-2-methylphenyl)-5-[2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-4(3H)-pyrimidinone (Compound 47) Step A: Preparation of N-(3-fluro-2-methylphenyl)benzenecarboximidamide sodium salt (1:1)

To a stirred solution of sodium bis(trimethylsilyl)amide (1.0 M in tetrahydrofuran, 200.0 mL, 200.0 mmol) was added 3-fluoro-2-methylaniline (25.0 g, 200.0 mmol) and allowed to stir for 10 min at room temperature. Benzonitrile (20.6 g, 200.0 mmol) was added, and the reaction mixture was stirred for 1 h at room temperature. The reaction mixture was concentrated and the solid that formed was filtered, washed with diethyl ether and dried under reduced pressure to afford the title product as a grey solid (51.0 g), which was used without further purification in the next step.

Step B: Preparation of 1-(3-fluoro-2-methylphenyl)-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylic acid

To a stirred solution of N-(3-fluro-2-methylphenyl)benzenecarboximidamide sodium salt (1:1) (i.e. the product from Example 5, Step A) (51.0 g, 200 mmol) in acetonitrile (300 mL) was added diethyl ethoxymethylenemalonate (44.04 g, 200 mmol). The reaction was stirred at room temperature for 30 min followed by the addition of water (3.6 mL, 200 mmol). The reaction was then stirred for another 30 min Water (100 mL) was added to the residue, followed by a saturated solution of sodium bicarbonate (300 mL), and the mixture was extracted with ethyl acetate. The aqueous layer was acidified with concentrated hydrochloric acid until the pH was 1-2, and the mixture was extracted with dichloromethane. The organic layer was dried (MgSO₄) and concentrated under reduced pressure to provide a solid, which was washed with diethyl ether and dried under reduced pressure to afford the title product as a off-white solid (18 g).

¹H NMR (CDCl₃) δ 12.68 (s, 1H), 9.15 (s, 1H), 7.43 (m, 1H), 7.19-7.38 (m, 5H), 7.12 (m, 1H), 6.88 (m, 1H), 2.03 (s, 3H).

Step C: Preparation of 3-oxo-1-cyclohexen-1-yl 1-(3-fluoro-2-methylphenyl)-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylate

To a stirred solution of 1-(3-fluoro-2-methylphenyl)-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylic acid (i.e. the product from Example 5, Step B) (41.0 g, 126 mmol) in dichloromethane (400 mL) was added oxalyl chloride (31.05 g, 252.0 mmol) at 0° C. followed by a catalytic amount (7 drops) of N,N-dimethylformamide. The reaction mixture was allowed to warm to room temperature and stir for 1 h. The reaction mixture was then concentrated under reduced pressure. To the resulting residue was added dichloromethane (400 mL), 1,3-cyclohexanedione (17.03 g, 152 mmol), followed by triethylamine (38.30 g, 379 mmol) and the reaction mixture was stirred at room temperature for 30 min. Saturated aqueous ammonium chloride solution was added, and the mixture was extracted with dichloromethane. The organic layer was washed once with water. Then the organic layer was dried (MgSO₄) and concentrated under reduced pressure. The resulting solid was washed with chlorobutane to afford the title product pure as an off-white solid (37.6 g).

¹H NMR (CDCl₃) δ 8.92 (s, 1H), 7.24-7.40 (m, 5H), 7.18 (m, 1H), 7.05 (m, 1H), 6.87 (m, 1H), 6.05 (s, 1H), 2.68 (m, 2H), 2.45 (m, 2H), 2.11 (m, 2H), 2.03 (s, 3H).

Step D: Preparation of 3-(3-fluoro-2-methylphenyl)-5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-4(3H)-pyrimidinone

To a stirred solution of 3-oxo-1-cyclohexen-1-yl 1-(3-fluoro-2-methylphenyl)-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylate (i.e. the product from Example 5, Step C) (42 g, 100.4 mmol) in acetonitrile (200 mL) was added cesium fluoride (30.5 g, 200.8 mmol). The reaction mixture was stirred for 24 h at room temperature. Water and ethyl acetate was added to the reaction mixture and the water layer was extracted several times with ethyl acetate. The combined organic layers were dried (MgSO₄) and concentrated under reduced pressure. The resulting solid was washed several times with ether and filtered, followed by the addition 60 mL of ethyl acetate and let stir for 2 h. The resulting solid was then washed again with ether and dried under reduced pressure to afford the title product, a compound of the present invention, as a yellow solid (26 g).

¹H NMR (CDCl₃) δ 16.38 (s, 1H), 8.28 (s, 1H), 7.21-7.34 (m, 5H), 7.11 (m, 1H), 7.00 (m, 1H), 6.86 (m, 1H), 2.70 (m, 2H), 2.47 (m, 2H), 2.10 (m, 3H), 2.03 (m, 2H).

Example 6 Preparation of 5-[5-cyclopropyl-4-isoxazolyl)carbonyl]-2,3-diphenyl-4(3H)-pyrimidinone (Compound 223) Step A: Preparation of 1-cyclopropyl-3-(1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinyl)-1,3-propanedione

To a mixture of 1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylic acid (i.e. the product from Example 1, step B) (1.84 g, 6.3 mmol) and toluene (6.3 mL) was added phosphorus pentachloride (1.31 g, 6.3 mmol) at ambient temperature. The resulting mixture was heated at reflux under a nitrogen atmosphere for 6 h. The resulting yellow solution was concentrated to give 1.53 g of the acid chloride as a yellow solid.

n-Butyllithium (2.5M solution in hexanes, 2.2 mL, 5.6 mmol) was added dropwise to a solution of N,N-diisopropylamine (0.82 mL, 5.8 mmol) and anhydrous tetrahydrofuran (8 mL) at −78° C. under a nitrogen atmosphere. The resulting solution was warmed to 0° C., stirred for 30 min, and then cooled to −78° C. Cyclopropyl methyl ketone (0.55 mL, 5.6 mmol) was added dropwise at below −65° C. The resulting solution was stirred at −78° C. for 30 min and was then treated with a slurry of the acid chloride as prepared above (823 mg, 2.7 mmol) in anhydrous tetrahydrofuran (5 mL) added dropwise via syringe at below 60° C. Additional anhydrous tetrahydrofuran (5 mL) was used to complete the transfer of the acid chloride. The resulting mixture was stirred at −78° C. for 1 h and was then treated with saturated aqueous ammonium chloride (7 mL) at below −50° C. The resulting mixture was stirred at ambient temperature for 15 min and was partitioned between ethyl acetate (100 mL) and saturated aqueous ammonium chloride (50 mL). The organic layer was dried over MgSO₄, filtered, and concentrated onto silica gel (2.5 g). The residue was purified by medium pressure liquid chromatography using a 24 g silica column and eluting with a gradient of 0 to 100% ethyl acetate in hexanes to provide the title compound as a pale yellow glassy solid (250 mg).

¹HNMR (400 MHz, CDCl₃) δ 15.88 (s, 1H), 8.93 (s, 1H), 7.40-7.33 (m, 3H), 7.33-7.26 (m, 3H), 7.24-7.19 (m, 3H), 7.14 (apparent d, 2H), 1.81 (sep, 1H), 1.20-1.15 (m, 2H), 0.99-0.92 (m, 2H).

Step B: Preparation of 1-cyclopropyl-3-(1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinyl)-2-(ethoxymethylene)-1,3-propanedione

A suspension of 1-cyclopropyl-3-(1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinyl)-1,3-propanedione (i.e. the product from Example 6, Step A) (165 mg, 0.46 mmol), triethyl orthoformate (0.23 mL, 1.4 mmol), and acetic anhydride (0.92 mL) was heated at 110° C. under a nitrogen atmosphere for 4 h. The residue was dissolved in toluene (5 mL) and the resulting solution was concentrated under reduced pressure at 50° C. The residue was re-dissolved in toluene (5 mL) and the resulting solution was concentrated at 50° C. to give 181 mg of the title compound as a brown oil that was used in the next step without further purification. ¹H NMR analysis showed the product to contain a mixture of Z- and E-olefin isomers.

¹HNMR (400 MHz, CDCl₃) 8.63 and 8.47 (2s, 1H total), 7.68 and 7.62 (2s, 1H total), 7.33-7.16 (m, 8H), 7.10-7.02 (m, 2H), 4.27 and 4.16 (2q, 2H total), 2.64-2.57 (m, <1H), 1.42 and 1.33 (3t, 3H total), 1.11-1.06 and 1.04-0.98 (2m, 2H total), 0.91-0.82 (m, 2H).

Step C: Preparation of 5-[(5-cyclopropyl-4-isoxazolyl)carbonyl]-2,3-diphenyl-4(3H)-pyrimidinone

Anhydrous sodium acetate (68 mg, 0.83 mmol) was added to a solution of 1-cyclopropyl-3-(1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinyl)-2-(ethoxymethylene)-1,3-propanedione (i.e. the product from Example 6, Step B) (171 mg, 0.41 mmol) in ethanol (4 mL) at 0° C. Hydroxylamine hydrochloride (29 mg, 0.42 mmol) was added and the resulting suspension was stirred at 0° C. for 30 min and then at ambient temperature for 2 h. The resulting mixture was diluted with ethyl acetate (20 mL) and ethanol (20 mL), concentrated onto 0.8 g silica gel, and the residue purified by medium pressure liquid chromatography using a 12 g silica gel column and eluting with 0 to 100% ethyl acetate in hexanes to obtain 14 mg of the title compound, a compound of the present invention as a yellow glassy solid. ¹HNMR (400 MHz, CDCl₃) 8.56 (s, 1H), 8.45 (s, 1H), 7.40-7.30 (m, 6H), 7.25-7.20 (m, 2H), 7.16-7.12 (m, 2H), 3.02-2.93 (m, 1H), 1.37-1.32 (m, 2H), 1.27-1.22 (m, 2H).

Example 7 Preparation of 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-3-phenyl-2-(3-pyridinyl)-4(3H)-pyrimidone (Compound 113) Step A: Preparation of N-phenyl-3-pyridinecarboximidamide

Sodium hydride (60% in mineral oil, 11.52 g, 288 mmol) was added portion-wise over 30 min to a stirred solution of 3-pyridinecarbonitrile (30 g, 288 mmol) and aniline (26 g, 290 mmol) in dimethylsulfoxide (150 mL) at 10° C. The reaction mixture was allowed to warm to ambient temperature with stirring for 18 h. The reaction mixture was slowly and cautiously poured into water containing crushed ice. The solid that precipitated was filtered, washed with petroleum ether, dissolved in dichloromethane and dried over anhydrous Na₂SO₄. The volatiles were removed under reduced pressure (high vacuum) and the residue was dried to afford 36.5 g of the title compound as a yellow solid.

¹H NMR (CDCl₃, 500 MHz) δ 9.06 (s, 1H), 8.68 (d, 1H), 8.22 (d, 1H), 7.38-7.35 (m, 3H), 7.08 (t, 1H), 6.97 (d, 2H), 5.00 (s, 2H).

Step B: Preparation of ethyl 1,6-dihydro-6-oxo-1-phenyl-2-(3-pyridinyl)-5-pyrimidinecarboxylate

A suspension of the N-phenyl-3-pyridinecarboximidamide (i.e. the product from Example 7, Step A) (36.5 g, 185 mmol) in diethyl ethoxymethylenemalonate (60 g, 280 mmol) was heated to 160° C. for 8 h. Ethanol formed in the reaction was collected using a distillation head attached to the flask containing the heated reaction mixture. The reaction mixture was then cooled to ambient temperature when the formation of a solid was observed. A mixture of diethyl ether/petroleum ether (8:2) was added to the reaction mixture was filtered. The collected solid was washed with additional ether/petroleum ether (4:1) followed by n-chlorobutane/petroleum ether (1:1) to obtain 51 g of the title compound as a light brown powder.

¹H NMR (CDCl₃, 500 MHz) δ 8.79 (s, 1H), 8.57 (dd, 1H), 8.52 (dd, 1H), 7.58 (dt, 1H), 7.38-7.35 (m, 3H), 7.16-7.13 (m, 3H), 4.41 (q, 2H), 1.39 (t, 3H).

Step C: Preparation of 1,6-dihydro-6-oxo-1-phenyl-2-(3-pyridinyl)-5-pyrimidinecarboxylic acid

A suspension of ethyl 1,6-dihydro-6-oxo-1-phenyl-2-(3-pyridinyl)-5-pyrimidinecarboxylate (i.e. the product from Example 7, Step B) (5.0 g, 15.5 mmol) and lithium iodide (powder, 5.2 g, 38.8 mmol) in pyridine (15 mL) was heated to 125-130° C. for 12 h. After cooling to ambient temperature, excess solvent was removed under reduced pressure. The resulting residue was dissolved in water (100 mL) and acidified with hydrochloric acid (6 N) to pH 7. The resulting dark brown solution was extracted with ethyl acetate (1×100 mL) to remove the non polar impurities. The aqueous layer was again extracted with dichloromethane/methanol (95:5) (2×50 mL). After initial extractions, the aqueous layer was slowly acidified to pH 4 and further extracted with dichloromethane/methanol (95:5) (3×50 mL). The combined neutral and acidic extracts were washed with brine and dried over anhydrous Na₂SO₄. The residue obtained after removal of the solvent was dried under high-vacuum to obtain 3.4 g of the title compound as a light brown solid.

¹H NMR (CDCl₃, 500 MHz) δ 12.67 (br s, 1H), 9.12 (s, 1H), 8.60-8.57 (m, 2H), 7.65 (dt, 1H), 7.47-7.46 (m, 3H), 7.22-7.19 (m, 3H).

Step D: Preparation of 3-oxo-1-cyclohexen-1-yl 1,6-dihydro-6-oxo-1-phenyl-2-(3-pyridinyl)-5-pyrimidinecarboxylate

To a stirred suspension of 1,6-dihydro-6-oxo-1-phenyl-2-(3-pyridinyl)-5-pyrimidinecarboxylic acid (i.e. the product from Example 7, Step C) (10.7 g, 36.3 mmol) in dichloromethane (150 mL) at ambient temperature was added 2-chloro-N-methyl pyridinium iodide (also known as the Mukaiyama reagent) (14.8 g, 57.9 mmol) followed by cyclohexanedione (6.5 g, 58 mmol) and triethylamine (9.2 g, 91 mmol). The reaction mixture was left stirring at ambient temperature overnight, then diluted with dichloromethane, washed with water, brine and dried over anhydrous Na₂SO₄. The residue obtained after removal of the solvent under vacuum was purified by tituration with n-chlorobutane/petroleum ether mixtures to obtain 9.8 g of the title compound as a light brown solid.

¹H NMR (CDCl₃, 500 MHz) δ 8.89 (s, 1H), 8.60 (d, 1H) 8.54 (dd, 1H), 7.61 (dt, 1H), 7.42-7.37 (m, 3H), 7.19-7.14 (m, 3H), 6.04 (s, 1H), 2.69-2.66 (m, 2H), 2.45-2.42 (m, 2H), 2.10 (q, 2H).

Step E: Preparation of 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-3-phenyl-2-(3-pyridinyl)-4(3H)-pyrimidone

To a stirred solution of 3-oxo-1-cyclohexen-1-yl 1,6-dihydro-6-oxo-1-phenyl-2-(3-pyridinyl)-5-pyrimidinecarboxylate (i.e. the product from Example 7, Step D) (11.1 g, 28.6 mmol) in acetonitrile (166 mL) was added cesium fluoride (8.71 g, 57.3 mmol) followed by catalytic amount (˜50 mg) of tetrabutylammonium bromide at ambient temperature. After stirring for 3 h at ambient temperature, the reaction mixture was diluted with ethyl acetate, washed with water, brine and dried over anhydrous Na₂SO₄. The volatile components were removed under reduced pressure and the residue was subjected to silica gel column chromatography eluting with ethyl acetate/petroleum ether (1:1) to ethyl acetate to dichloromethane/methanol (95:5). The product obtained was washed with minimum amount of methanol to afford 1.4 g of the title compound, a compound of the present invention as a light yellow solid.

¹H NMR (CDCl₃, 500 MHz) mixture of tautomers δ 16.45 (s, 0.8H), 8.57-8.50 (m, 2H), 8.21 (s, 1H), 7.57 (d, 1H), 7.35 (d, 3H), 7.16-7.13 (m, 3H), 5.29 (s, 0.2H,), 2.71 (br s, 2H), 2.47 (br s, 2H), 2.04-2.02 (m, 2H).

Example 8 Preparation of 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-3-(cis/trans-tetrahydro-1-oxido-2H-thiopyran-4-yl)-4(3H)-pyrimidinone (Compound 168) and 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-3-(trans/cis-tetrahydro-1-oxido-2H-thiopyran-4-yl)-4(3H)-pyrimidinone (Compound 169) Step A: Preparation of 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-3-(cis/trans-tetrahydro-1-oxido-2H-thiopyran-4-yl)-4(3H)-pyrimidinone and 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-3-(trans/cis-tetrahydro-1-oxido-2H-thiopyran-4-yl)-4(3H)-pyrimidinone

To 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-3-(tetrahydro-2H-thiopyran-4-yl)-4(3H)-pyrimidinone (the tautomer known as 2-[[1,6-dihydro-6-oxo-2-phenyl-1-(tetrahydro-2H-thiopyran-4-yl)-5-pyrimidinyl]carbonyl]-1,3-cyclohexanedione) (0.15 g, 0.37 mmol) in a mixture of 5.0 mL water and 5.0 mL methanol at room temperature was added NaIO₄ (0.074 g, 0.35 mmol). After approximately 45 min, additional NaIO₄ (0.011 g, 0.05 mmol) was added and stirring was continued for an additional 2 h. The reaction mixture was extracted with dichloromethane and the combined organics were dried over MgSO₄ concentrated under reduced pressure and purified by medium pressure liquid chromatography on silica gel eluting with 0 to 10% methanol in chloroform to provide 0.07 g of Compound 168 (alternatively known as 2-[[1,6-dihydro-6-oxo-2-phenyl-1-(cis/trans-tetrahydro-1-oxido-2H-thiopyran-4-yl)-5-pyrimidinyl]carbonyl]-1,3-cyclohexanedione) and and 0.03 g of Compound 169 (alternatively known as 2-[[1,6-dihydro-6-oxo-2-phenyl-1-(trans/cis-tetrahydro-1-oxido-2H-thiopyran-4-yl)-5-pyrimidinyl]carbonyl]-1,3-cyclohexanedione) both as solids.

¹H NMR of Compound 168 (CDCl₃) δ 16.58 (br s, 1H), 7.99 (s, 1H), 7.58 (m, 3H), 7.47 (m, 2H), 4.14 (m, 1H), 3.39 (m, 2H), 3.12 (m, 2H), 2.74 (t, 2H), 2.49 (t, 2H), 2.37 (t, 2H), 2.05 (m, 4H).

¹H NMR Compound 169 (CDCl₃) δ 16.42 (br s, 1H), 8.00 (s, 1H), 7.54 (m, 5H), 4.06 (m, 1H), 3.65 (m, 2H), 3.07 (m, 2H), 2.60 (br s, 4H), 2.17 (m, 2H), 2.07 (m, 2H), 1.80 (d, 2H).

Example 9 Preparation of 2-(3,5-difluorophenyl)-5-[(2-hydroxy-4-oxobicyclo[3.2.1]oct-2-en-3-yl)carbonyl]-3-(2-methoxyethyl)-4(3H)-pyrimidinone (Compound 243) Step A: Preparation of 3,5-difluorobenzenecarboxamidic acid ethyl ester hydrochloride (1:1)

To a stirred solution of 3,5-difluorobenzonitirile (25 g, 180 mmol) in ethanol (336 mL) and dichloromethane (180 mL) at 0° C., was added acetyl chloride (128 mL, 1800 mmol) drop wise via addition funnel. The reaction mixture was allowed to warm to room temperature and stir for 24 h. The reaction mixture was then concentrated under reduced pressure to afford a solid, which was washed with diethyl ether and dried under reduced pressure to afford the title product as a white solid (21.5 g) which was carried forward to the next step without further purification.

Step B: Preparation of 3,5-difluoro-N-(2-methoxyethyl)benzenecarboximidamide hydrochloride (1:1)

To a stirred solution of 3,5-difluorobenzenecarboxamidic acid ethyl ester hydrochloride (5.39 g, 24.3 mmol) (i.e. the product from Example 9, Step A) in methanol (25 mL) at 0° C., was added 2-methoxy-1-ethylamine (2.2 mL, 25.5 mmol). The reaction mixture was allowed to warm to room temperature and stir for 24 h. The reaction mixture was concentrated under reduced pressure to afford the title product as a gummy oil, which was used without further purification in the next step.

Step C: Preparation of ethyl 2-(3,5-difluorophenyl)-1,6-dihydro-1-(2-methoxyethyl)-6-oxo-5-pyrimidinecarboxyate

To a stirred solution of 3,5-difluoro-N-(2-methoxyethyl)benzenecarboximidamide hydrochloride (1:1 (i.e. the product from Example 9, Step B) (24.3 mmol) in ethanol (25 mL) was added diethyl ethoxymethylenemalonate (5.25 g, 24.3 mmol) followed by sodium ethoxide (21% soln) (9.1 mL, 24.3 mmol). The reaction mixture was heated and stirred at reflux for 24 h. The reaction mixture was cooled to room temperature concentrated under reduced pressure. The residue was purified by column chromatography eluting with 50% ethyl acetate in hexanes to afford the title product as a white solid (6.1 g).

¹H NMR (CDCl₃) δ 8.65 (s, 1H), 7.14 (m, 2H), 6.98 (m, 1H), 4.41 (m, 2H), 4.21 (m, 2H), 3.67 (m, 2H), 3.22 (s, 3H), 1.40 (m, 3H).

Step D: Preparation of 2-(3,5-difluorophenyl)-1,6-dihydro-1-(2-methoxyethyl)-6-oxo-5-pyrimidinecarboxylic acid

To a stirred solution of ethyl ethyl 2-(3,5-difluorophenyl)-1,6-dihydro-1-(2-methoxyethyl)-6-oxo-5-pyrimidinecarboxyate (i.e. the product from Example 9, Step C) (1.14 g, 3.37 mmol) in ethyl acetate (10 mL) was added lithium iodide powder (1.35 g, 10.0 mmol). The reaction mixture was heated to reflux for 24 h, cooled, and then stirred at room temperature for 72 h. The reaction mixture was concentrated under reduced pressure. To the resulting residue was added water (10 mL), followed by 6 N hydrochloric acid until the pH was 2. The mixture was extracted with dichloromethane, and the organic layer was dried (MgSO₄) and concentrated under reduced pressure to afford a solid, which was washed with diethyl ether and dried under reduced pressure to afford the title product as a white solid (700 mg).

¹H NMR (CDCl₃) δ 12.88 (s, 1H), 8.99 (s, 1H), 7.20 (m, 2H), 7.03 (m, 1H), 4.32 (m, 2H), 3.69 (m, 2H), 3.25 (s, 3H).

Step E: Preparation of 2-(3,5-difluorophenyl)-5-[(2-hydroxy-4-oxobicyclo[3.2.1]oct-2-en-3-yl)carbonyl]-3-(2-methoxyethyl)-4(3H)-pyrimidinone

To 2-(3,5-difluorophenyl)-1,6-dihydro-1-(2-methoxyethyl)-6-oxo-5-pyrimidinecarboxylic acid (i.e. the product from Example 9, Step D) (0.25 g, 0.81 mmol) in 10 mL of dichloromethane was added oxalyl chloride (0.21 g, 1.6 mmol) and one drop of N,N-dimethylformamide. The reaction mixture was stirred at room temperature for 2 h and then concentrated under reduced pressure. The remaining crude oil was re-dissolved in dichloromethane (10 mL) and then treated with bicycle[3.2.1]octane-2,4-dione (0.12 g, 0.88 mmol) (prepared according to U.S. Pat. No. 6,815,563) and triethylamine (0.16 g, 1.6 mmol). After 30 min at room temperature, a catalytic amount of 2-hydroxy-2-methyl-propanenitrile (0.0075 g, 0.088 mmol) and triethylamine (0.16 g, 1.6 mmol) were added and the reaction mixture was stirred at ambient temperature over night. The reaction mixture was then concentrated under reduced pressure and purified by medium pressure liquid chromatography on silica gel eluting with 0 to 10% methanol in chloroform to provide 0.180 g of the title compound (also known as 3-[[2-(3,5-difluorophenyl)-1,6-dihydro-1-(2-methoxyethyl)-6-oxo-5-pyrimidinyl]carbonyl]biciclo[3.2.1]octane-2,4-dione), a compound of the present invention, as a solid.

¹H NMR (CDCl₃) δ 16.58 (br s, 1H), 8.05 (s, 1H), 7.17 (m, 2H), 6.96 (m, 1H), 4.18 (br s, 2H), 3.61 (t, 2H), 3.26 (br s, 3H), 3.09 (br s, 1H), 2.96 (br s, 1H), 2.26 (d, 1H), 2.17 (br s, 2H), 2.02 (br s, 1H), 1.88 (br s, 1H), 1.73 (m, 1H).

Example 10 Preparation of 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-3-(2-methoxyethyl)-2-(3-thienyl)-4(3H)-pyrimidinone (Compound 97) Step A: Preparation of 3-thiophenecarboximidic acid ethyl ester hydrochloride

To a solution of thiophene-3-carbonitrile (10 g, 9.2 mmol) in dichloromethane (100 mL) and ethanol (170 mL) at 0° C. was added acetyl chloride (114 g, 145 mmol). The reaction was allowed to slowly warm to ambient temperature and stir 16 h. The reaction mixture was then concentrated under reduced pressure to yield a solid which was triturated with diethyl ether resulting in 17.1 g of 3-thiophenecarboximidic acid ethyl ester hydrochloride as a white solid.

¹H NMR (DMSO-d₆) δ 11.77 (br s, 2H), 8.92 (m, 1H), 7.90 (m, 1H), 7.83 (m, 1H), 4.60 (q, 2H), 1.46 (t, 3H).

Step B: Preparation of ethyl 1,6-dihydro-1-(2-methoxyethyl)-6-oxo-2-(3-thienyl)-5-pyrimidinecarboxylate

2-Methoxy-1-ethylamine (0.86 g, 11.4 mmol) was added to a solution of 3-thiophenecarboximidic acid ethyl ester hydrochloride (2.0 g, 10.4 mmol) in methanol (10 mL), which was then stirred at ambient temperature for 1.5 h. The reaction mixture was then concentrated under reduced pressure and redissolved in ethanol (10 mL). Sodium ethoxide solution (21% w/w in ethanol, 3.4 g, 10 mmol) and diethyl ethoxymethylenemalonate (2.2 g, 10 mmol) were added and the mixture was heated to reflux for 2 h before being concentrated under reduced pressure and purified by medium pressure liquid chromatography on silica gel eluting with 0 to 100% ethyl acetate in hexanes to provide 1.82 g of the title compound as an oil.

¹H NMR (CDCl₃) δ 8.68 (s, 1H), 8.06 (m, 1H), 7.48 (m, 1H), 7.43 (m, 1H), 4.38 (m, 4H), 3.81 (t, 2H), 3.29 (s, 3H), 1.40 (t, 3H).

Step C: 1,6-dihydro-1-(2-methoxyethyl)-6-oxo-2-(3-thienyl)-5-pyrimidinecarboxylic acid

Ethyl 1,6-dihydro-1-(2-methoxyethyl)-6-oxo-2-(3-thienyl)-5-pyrimidinecarboxylate a (1.82 g, 5.90 mmol) (i.e. the product from Example 10, Step B) was dissolved in ethyl acetate and treated with lithium iodide (powder, 2.36 g, 17.6 mmol) and heated to reflux for 16 h. The crude reaction mixture was concentrated under reduced pressure and then aqueous sodium bicarbonate solution was added and the resulting solution was extracted with ethyl acetate which was then discarded. The aqueous layer was made acidic with hydrochloric acid (1 N) and then extracted with dichloromethane (2×40 mL). The combined organics were dried over MgSO₄ and concentrated under reduced pressure to provide the title compound as a solid.

¹H NMR (CDCl₃) δ 12.96 (br s, 1H), 8.99 (s, 1H), 8.17 (m, 1H), 7.53 (m, 1H), 7.48 (m, 1H), 4.47 (t, 2H), 3.83 (t, 2H), 3.32 (s, 3H).

Step D: Preparation of 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-3-(2-methoxyethyl)-2-(3-thienyl)-4(3H)-pyrimidinone

To 1,6-dihydro-1-(2-methoxyethyl)-6-oxo-2-(3-thienyl)-5-pyrimidinecarboxylic acid (i.e. the product from Example 10, Step C) (0.5 g, 1.8 mmol) in 10 mL of dichloromethane was added oxalyl chloride (0.45 g, 3.6 mmol) and one drop of N,N-dimethylformamide. The reaction mixture was stirred at room temperature for 2 h and then concentrated under reduced pressure. The crude oil was redissolved in 10 mL of dichloromethane and treated with 1,3-cyclohexanedione (0.22 g, 2.0 mmol) and triethylamine (0.18 g, 1.8 mmol). The reaction mixture was stirred for 30 min then treated with a catalytic amount of 2-hydroxy-2-methyl-propanenitrile (0.015 g, 0.18 mmol) and triethylamine (0.182 g, 1.8 mmol) and stirred at ambient temperature for 16 h. The reaction mixture was then concentrated under reduced pressure and purified by medium pressure liquid chromatography on silica gel eluting with 0 to 10% methanol in chloroform to provide 0.160 g of the title compound (also known as 2-[[1,6-dihydro-1-(2-methoxyethyl)-6-oxo-2-(3-thienyl)-5-pyrimidinyl]carbonyl]-1,3-cyclohexanedione), a compound of the invention, as a solid.

¹H NMR (CDCl₃) δ 16.51 (s, 1H), 8.14 (s, 1H), 7.97 (m, 1H), 7.43 (m, 2H), 4.29 (t, 2H), 3.70 (t, 2H), 3.29 (s, 3H), 2.73 (t, 2H), 2.50 (t, 2H), 2.08 (m, 2H).

Example 11 Preparation of 3-cyclohexyl-5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-4(3H)-pyrimidinone (Compound 128) Step A: Preparation of ethyl 1-cyclohexyl-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxyate

Cyclohexylamine (0.58 g, 5.8 mmol) was added to a solution of ethyl benzenecarboximidic acid ethyl ester (1.0 g, 5.4 mmol) in methanol (10 mL), which was then stirred at room temperature for 16 h. The reaction mixture was then concentrated under reduced pressure and then redissolved in ethanol (10 mL). Sodium ethoxide solution (21% w/w in ethanol, 1.8 g, 5.5 mmol) and diethyl ethoxymethylenemalonate (1.2 g, 5.5 mmol) were added and the mixture was heated to reflux for 16 h before being concentrated under reduced pressure and purified by medium pressure liquid chromatography on silica gel eluting with 0 to 100% ethyl acetate in hexanes to provide 1.41 g of the title compound as a yellow oil.

¹H NMR (CDCl₃) δ 8.58 (s, 1H), 7.53 (m, 3H), 7.45 (m, 2H), 4.41 (m, 2H), 3.94 (m, 1H), 2.76 (m, 2H), 1.78 (d, 2H), 1.67 (d, 2H), 1.53 (d, 1H), 1.42 (m, 3H), 1.21 (m, 1H), 0.96 (m, 2H).

Step B: Preparation of 1-cyclohexyl-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylic acid

Ethyl 1-cyclohexyl-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxyate (1.41 g, 4.32 mmol) (i.e. the product from Example 11, Step A) was dissolved in ethyl acetate and treated with lithium iodide (powder, 1.72 g, 12.8 mmol) and heated to reflux for 16 h. The crude reaction mixture was concentrated under reduced pressure and then aqueous sodium bicarbonate was added and the resulting solution was extracted with ethyl acetate which was then discarded. The aqueous layer was made acidic with hydrochloric acid (1 N) and then extracted with dichloromethane (2×40 mL). The combined organic extracts were dried over MgSO₄ and concentrated under reduced pressure resulting in 0.58 g of the title product as a solid.

¹H NMR (CDCl₃) δ 13.30 (br. s., 1H), 8.94 (s, 1H), 7.59 (m, 3H), 7.48 (m, 2H), 4.12 (m, 1H), 2.68 (m, 2H), 1.84 (d, 2H), 1.74 (d, 2H), 1.60 (d, 1H), 1.22 (m, 1H), 1.03 (m, 2H).

Step C: Preparation of 2-[(1-cyclohexyl-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinyl)carbonyl]-1,3-cyclohexanedione

To 1-cyclohexyl-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylic acid (i.e. the product from Example 11, Step B) (0.58 g, 1.5 mmol) in 10 mL of dichloromethane was added oxalyl chloride (0.490 g, 3.9 mmol) and one drop of N,N-dimethylformamide. The reaction was stirred at ambient temperature for 2 h and then concentrated under reduced pressure. The crude oil was then redissolved in 10 mL of dichloromethane and then treated with 1,3-cyclohexanedione (0.24 g, 2.1 mmol) and triethylamine (0.39 g, 3.8 mmol) stirred for 30 min, then treated with a catalytic amount of 2-hydroxy-2-methyl-propanenitrile (0.015 g, 0.15 mmol) and triethylamine (0.393 g, 3.8 mmol) and stirred at ambient temperature for 16 h. The reaction mixture was then concentrated under reduced pressure and purified by medium pressure liquid chromatography on silica gel eluting with 0 to 10% methanol in chloroform to provide 0.570 g of the title compound, a compound of the invention, as a solid.

¹H NMR (CDCl₃) δ 16.61 (s, 1H), 8.02 (s, 1H), 7.50 (m, 5H), 3.93 (m, 1H), 2.73 (t, 2H), 2.61 (m, 2H), 2.51 (t, 2H), 2.08 (m, 2H), 1.74 (m, 4H), 1.51 (d, 1H), 1.19 (m, 1H), 0.97 (m, 2H).

By the procedures described herein together with methods known in the art, the following compounds of Tables 1 to 32 can be prepared. The following abbreviations are used in the Tables which follow: Me means methyl, Et means ethyl, n-Pr means normal propyl, i-Pr means isopropyl, c-Pr means cyclopropyl, n-Bu means normal butyl, i-Bu means isobutyl, s-Bu means secondary butyl, c-Bu means cyclobutyl, t-Bu means tertiary butyl, n-pent means normal pentyl, c-Pent means cyclopentyl, n-Hex means normal hexyl, hept means hetpyl, c-Hex means cyclohexyl, Ph means phenyl, OMe means methoxy, OEt means ethoxy, SMe means methylthio, SEt means ethylthio, thp means tetrahydropyran, thtp means tetrahydrothiopyran, thf means tetrahydrofuran, —CN means cyano, —NO₂ means nitro, S(O)Me means methylsulfinyl, SO₂ means sulfonyl and S(O)₂Me means methylsulfonyl.

TABLE 1

R² is Ph R¹ Me Et n-Pr i-Pr c-Pr n-Bu i-Bu s-Bu c-Bu t-Bu n-pent c-Pent n-Hex c-Hex Ph CH₂-c-Pr CH₂-c-Bu CH₂SPh CH₂SCH₃ CH₂CF₃ CH₂Ph Ph(4-Me) CH₂CHC(CH₃)₂ CH₂CH₂C≡CH CH₂CH═CCl₂ CH₂CH═CF₂ CH₂CF═CF₂ CH₂CCl═CCl₂ CH₂C═CCH₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ CH₂SO₂CH₃ CH₂SCH₂CH₃ Ph(2,3-di-OMe) CH₂SO₂-n-Pr CH₂CH₂SO₂Et Ph(2,4-di-OMe) Ph(2,5-di-OMe) Ph(2,6-di-OMe) Ph(3,5-di-OMe) CH₂Ph(2-OMe) CH₂Ph(3-OMe) CH₂Ph(4-OMe) CH₂CH₂SMe CH₂SCH₂Ph CH₂SO₂Ph CH₂CH₂SEt Ph(2,4-di-Cl) Ph(2,5-di-Cl) Ph(2,6-di-Cl) Ph(3,5-di-Cl) Ph(2,3-di-Me) Ph(2,4-di-Me) Ph(2,5-di-Me) Ph(2,6-di-Me) Ph(3,5-di-Me) CH₂-c-Hex Ph(2,3-di-F) Ph(2,4-di-F) Ph(2,5-di-F) Ph(2,6-di-F) CH₂CH₂CF₃ CH₂C≡CH Ph(2,3-di-Cl) Ph(3,5-di-F) isoxazolin-2-yl Ph(2-Cl) Ph(3-Cl) Ph(4-Cl) Ph(2-Me) Ph(3-Me) CH₂OCH₃ CH₂CH═CH₂ Ph(2-OMe) Ph(3-OMe) Ph(4-OMe) Ph(2-CN) Ph(3-CN) Ph(4-CN) Ph(2-F) Ph(3-F) Ph(4-F) CH₂S-n-Pr CH₂-c-Pent oxazolin-2-yl 2-pyridinyl 3-pyridinyl 4-pyridinyl Ph(2-NO₂) Ph(3-NO₂) Ph(4-NO₂) Ph(2-CF₃) Ph(3-CF₃) Ph(4-CF₃) Ph(2-Br) Ph(3-Br) Ph(4-Br) CH₂Ph(2-Me) CH₂Ph(3-Me) CH₂Ph(4-Me) CH₂Ph(2-Cl) CH₂Ph(3-Cl) CH₂Ph(4-Cl) thiazol-3-yl thiazol-2-yl thiazolin-2-yl thiazol-2-yl oxazol-2-yl CH₂CF₂CF₃ CH═CH₂ CH₂(thf-2-yl) CH₂(3-methylisoxazolin-5-yl) isoxazolin-4-yl CH₂(3-methylisoxazol-5-yl) 5-methylisoxazol-3-yl 4-methyloxazol-2-yl 4-methylthiazol-2-yl CH₂CH₂CH═CH₂ CH₂SO₂CH₂CH₃ CH₂CH₂SO₂Me CH₂OCH₂OCH₃ 3-methylthiazol-2-yl 5-chloropyridin-2-yl 5-methylpyridin-2-yl 5-methoxypyridin-2-yl 6-methylpyridin-2-yl 6-methylpyridin-3-yl 3-methoxypyridin-4-yl 3-methylpyridin-4-yl 3-chloropyridin-4-yl CH₂OCH₂CH₂OCH₃ CH₂C(CH₃)C(CH₃)₂ n-hept c-hept thp-4-yl thtp-4-yl Ph(2,3-di-OMe) Ph(3,4-di-OMe) Ph(3,4-di-Me) Ph(3,4-di-F) Ph(3,4,5-tri-OMe) Ph(2-I) Ph(3-I) Ph(4-I) Ph(2-Et) Ph(3-Et) Ph(4-Et) CH₂CH₂OCH₂CH₃ CH(CH₃)CH₂OCH₃ Ph(2-OCF₃) Ph(3-OCF₃) Ph(4-OCF₃) Ph(2-Me-3-F) Ph(2-Me-4-F) Ph(2-Me-5-F) Ph(2-F-3-Me) Ph(2-F-4-Me) Ph(2-F-5-Me) Ph(3-F-4-Me) Ph(3-F-5-Me) Ph(3-Me-4-F) CH₂CH₂CH₂OCH₃ CH₂CH₂CH₂OCH₂CH₃ CH₂(thp-2-yl) CH₂(thp-4-yl) CH₂CH₂CH═CH₂ CH₂C≡CH CH₂CH₂SCH₃ CH₂CH₂SOCH₃ CH₂CH₂SO₂CH₃ CH₂CH₂CH₂SCH₃ CH₂CH₂CH₂SOCH₃ CH₂CH₂CH₂SO₂CH₃ c-hex(3-OCH₃) c-hex(4-OCH₃) c-hex(3,4-di-OCH₃) c-hex(3,5-di-OCH₃) CH₂CH₂SCH₃ The present disclosure also includes Tables 1A through 57A, each of which is constructed the same as Table 1 above except that the row heading in Table 1 (i.e. “R² is Ph”) is replaced with the respective row headings shown below. For example, in Table 1A the row heading is “R² is Me”, and R¹ is as defined in Table 1 above. Thus, the first entry in Table 1A specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R¹ is Me; R² is Me; R³ is OH; A is A-1; B¹ is C-1; B² is C-3; B³ is C-1; and each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is H. Tables 2A through 57A are constructed similarly.

Table Row Heading  1A R² is Me  2A R² is Et  3A R² is n-Pr  4A R² is c-Pr  5A R² is SMe  6A R² is SO₂Me  7A R² is CF₃  8A R² is Ph(2-Cl)  9A R² is Ph(3-Cl) 10A R² is Ph(4-Cl) 11A R² is Ph(2-Me) 12A R² is Ph(3-Me) 13A R² is Ph(4-Me) 14A R² is Ph(2-OMe) 15A R² is Ph(3-OMe) 16A R² is Ph(4-OMe) 17A R² is Ph(2-F) 18A R² is Ph(3-F) 19A R² is Ph(4-F) 20A R² is OMe 21A R² is OEt 22A R² is CH₂Ph 23A R² is 2-pyridinyl 24A R² is 3-pyridinyl 25A R² is 4-pyridinyl 26A R² is H 27A R² is Ph(3,5-di-F) 28A R² is Ph(3,4-di-F) 29A R² is Ph(3,4,5-tri-F) 30A R² is Ph(2,3-di-F) 31A R² is Ph(3-CF₃) 32A R² is Ph(4-CF₃) 33A R² is Ph(3,5-di-CF₃) 34A R² is n-Bu 35A R² is CH₂OCH₃, 36A R² is CH₂CH₂OCH₃ 37A R² is CH₂CH₂CF₃ 38A R² is CH₂CF₃ 39A R² is n-pent 40A R² is c-pent 41A R² is c-Hex 42A R² is n-Hex 43A R² is thp-4-yl 44A R² is Ph(2-CN) 45A R² is Ph(3-CN) 46A R² is Ph(4-CN) 47A R² is Ph(2-C≡CH) 48A R² is Ph(3-C≡CH) 49A R² is Ph(4-C≡CH) 50A R² is Ph(3-Me, 2-F) 51A R² is Ph(3-Me-4-F) 52A R² is Ph(3-Me, 5-F) 53A R² is Ph(3-Me, 6-F) 54A R² is Ph(3-F, 2-Me) 55A R² is Ph(3-F-4-Me) 56A R² is Ph(3-F-5-Me) 57A R² is Ph(3-F, 6-Me)

TABLE 2

R¹ is Me R² R³ R^(14a) R^(15a) R¹⁸ R¹⁹ R^(14b) R^(15b) Et OH Me H H H H H CF₃ OH Me H H H H H n-Pr OH Me H H H H H c-Pr OH Me H H H H H Ph OH Me H H H H H Ph(2-Cl) OH Me H H H H H Ph(3-Cl) OH Me H H H H H Ph(4-Cl) OH Me H H H H H SMe OH Me H H H H H SO₂Me OH Me H H H H H n-Bu OH Me H H H H H Ph(2-F) OH Me H H H H H Ph(3-F) OH Me H H H H H Ph(4-F) OH Me H H H H H Ph(3,5-di-F) OH Me H H H H H Ph(2-Me) OH Me H H H H H Ph(3-Me) OH Me H H H H H Ph(4-Me) OH Me H H H H H Ph(3,5-di-Me) OH Me H H H H H 2-pyridinyl OH Me H H H H H 3-pyridinyl OH Me H H H H H 4-pyridinyl OH Me H H H H H Et OH Me Me H H H H CF₃ OH Me Me H H H H n-Pr OH Me Me H H H H c-Pr OH Me Me H H H H Ph OH Me Me H H H H Ph(2-Cl) OH Me Me H H H H Ph(3-Cl) OH Me Me H H H H Ph(4-Cl) OH Me Me H H H H SMe OH Me Me H H H H SO₂Me OH Me Me H H H H Et OH H H Me Me H H CF₃ OH H H Me Me H H n-Pr OH H H Me Me H H c-Pr OH H H Me Me H H Ph OH H H Me Me H H Ph(2-Cl) OH H H Me Me H H Ph(3-Cl) OH H H Me Me H H Ph(4-Cl) OH H H Me Me H H SMe OH H H Me Me H H SO₂Me OH H H Me Me H H n-Bu OH H H Me Me H H Ph(2-F) OH H H Me Me H H Ph(3-F) OH H H Me Me H H Ph(4-F) OH H H Me Me H H Ph(3,5-di-F) OH H H Me Me H H Ph(2-Me) OH H H Me Me H H Ph(3-Me) OH H H Me Me H H Ph(4-Me) OH H H Me Me H H Ph(3,5-di-Me) OH H H Me Me H H 2-pyridinyl OH H H Me Me H H 3-pyridinyl OH H H Me Me H H 4-pyridinyl OH H H Me Me H H Et OH Me Me H H Me Me CF₃ OH Me Me H H Me Me n-Pr OH Me Me H H Me Me c-Pr OH Me Me H H Me Me Ph OH Me Me H H Me Me Ph(2-Cl) OH Me Me H H Me Me Ph(3-Cl) OH Me Me H H Me Me Ph(4-Cl) OH Me Me H H Me Me SMe OH Me Me H H Me Me SO₂Me OH Me Me H H Me Me n-Bu OH Me Me H H Me Me Ph(2-F) OH Me Me H H Me Me Ph(3-F) OH Me Me H H Me Me Ph(4-F) OH Me Me H H Me Me Ph(3,5-di-F) OH Me Me H H Me Me Ph(2-Me) OH Me Me H H Me Me Ph(3-Me) OH Me Me H H Me Me Ph(4-Me) OH Me Me H H Me Me Ph(3,5-di-Me) OH Me Me H H Me Me 2-pyridinyl OH Me Me H H Me Me 3-pyridinyl OH Me Me H H Me Me 4-pyridinyl OH Me Me H H Me Me Et SPh H H H H H H CF3 SPh H H H H H H n-Pr SPh H H H H H H c-Pr SPh H H H H H H Ph SPh H H H H H H Ph(2-Cl) SPh H H H H H H Ph(3-Cl) SPh H H H H H H Ph(4-Cl) SPh H H H H H H SMe SPh H H H H H H SO₂Me SPh H H H H H H n-Bu SPh H H H H H H Ph(2-F) SPh H H H H H H Ph(3-F) SPh H H H H H H Ph(4-F) SPh H H H H H H Ph(3,5-di-F) SPh H H H H H H Ph(2-Me) SPh H H H H H H Ph(3-Me) SPh H H H H H H Ph(4-Me) SPh H H H H H H Ph(3,5-di-Me) SPh H H H H H H 2-pyridinyl SPh H H H H H H 3-pyridinyl SPh H H H H H H 4-pyridinyl SPh H H H H H H Et OMe H H H H H H CF₃ OMe H H H H H H n-Pr OMe H H H H H H c-Pr OMe H H H H H H Ph OMe H H H H H H Ph(2-Cl) OMe H H H H H H Ph(3-Cl) OMe H H H H H H Ph(4-Cl) OMe H H H H H H SMe OMe H H H H H H SO₂Me OMe H H H H H H n-Bu OMe H H H H H H Ph(2-F) OMe H H H H H H Ph(3-F) OMe H H H H H H Ph(4-F) OMe H H H H H H Ph(3,5-di-F) OMe H H H H H H Ph(2-Me) OMe H H H H H H Ph(3-Me) OMe H H H H H H Ph(4-Me) OMe H H H H H H Ph(3,5-di-Me) OMe H H H H H H 2-pyridinyl OMe H H H H H H 3-pyridinyl OMe H H H H H H 4-pyridinyl OMe H H H H H H Et OSO₂Ph(4-Me) H H H H H H CF₃ OSO₂Ph(4-Me) H H H H H H n-Pr OSO₂Ph(4-Me) H H H H H H c-Pr OSO₂Ph(4-Me) H H H H H H Ph OSO₂Ph(4-Me) H H H H H H Ph(2-Cl) OSO₂Ph(4-Me) H H H H H H Ph(3-Cl) OSO₂Ph(4-Me) H H H H H H Ph(4-Cl) OSO₂Ph(4-Me) H H H H H H SMe OSO₂Ph(4-Me) H H H H H H SO₂Me OSO₂Ph(4-Me) H H H H H H n-Bu OSO₂Ph(4-Me) H H H H H H Ph(2-F) OSO₂Ph(4-Me) H H H H H H Ph(3-F) OSO₂Ph(4-Me) H H H H H H Ph(4-F) OSO₂Ph(4-Me) H H H H H H Ph(3,5-di-F) OSO₂Ph(4-Me) H H H H H H Ph(2-Me) OSO₂Ph(4-Me) H H H H H H Ph(3-Me) OSO₂Ph(4-Me) H H H H H H Ph(4-Me) OSO₂Ph(4-Me) H H H H H H Ph(3,5-di-Me) OSO₂Ph(4-Me) H H H H H H 2-pyridinyl OSO₂Ph(4-Me) H H H H H H 3-pyridinyl OSO₂Ph(4-Me) H H H H H H 4-pyridinyl OSO₂Ph(4-Me) H H H H H H Et OH Me Me —C(O)— Me Me CF₃ OH Me Me —C(O)— Me Me n-Pr OH Me Me —C(O)— Me Me c-Pr OH Me Me —C(O)— Me Me Ph OH Me Me —C(O)— Me Me Ph(2-Cl) OH Me Me —C(O)— Me Me Ph(3-Cl) OH Me Me —C(O)— Me Me Ph(4-Cl) OH Me Me —C(O)— Me Me SMe OH Me Me —C(O)— Me Me SO₂Me OH Me Me —C(O)— Me Me n-Bu OH Me Me —C(O)— Me Me Ph(2-F) OH Me Me —C(O)— Me Me Ph(3-F) OH Me Me —C(O)— Me Me Ph(4-F) OH Me Me —C(O)— Me Me Ph(3,5-di-F) OH Me Me —C(O)— Me Me Ph(2-Me) OH Me Me —C(O)— Me Me Ph(3-Me) OH Me Me —C(O)— Me Me Ph(4-Me) OH Me Me —C(O)— Me Me Ph(3,5-di-Me) OH Me Me —C(O)— Me Me 2-pyridinyl OH Me Me —C(O)— Me Me 3-pyridinyl OH Me M —C(O)— Me Me 4-pyridinyl OH Me Me —C(O)— Me Me The present disclosure also includes Tables 1B through 38B, each of which is constructed the same as Table 2 above except that the row heading in Table 2 (i.e. “R¹ is Me”) is replaced with the respective row headings shown below. For example, in Table 1B the row heading is “R¹ is Et”, and R², R³, R^(14a), R^(15a), R¹⁸, R¹⁹, R^(14b) and R^(15b) are as defined in Table 2 above. Thus, the first entry in Table 1B specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R¹ is Et; R² is Et, R³ is OH; A is A-1; B¹ is C-1, B² is C-3 and B³ is C-1; R^(14a) is Me; R^(15a) is H; R¹⁸ is H; R¹⁹ is H; R^(14b) is H; and R^(15b) is H. Tables 2B through 38B are constructed similarly.

Table Row Heading  1B R¹ is Et  2B R¹ is CH₂CF₃  3B R¹ is CH₂CH═CH₂  4B R¹ is CH₂C≡CH  5B R¹ is Ph  6B R¹ is Ph(2-Me)  7B R¹ is Ph(4-Me)  8B R¹ is Ph(2-Cl)  9B R¹ is Ph(3-Cl) 10B R¹ is n-Pr 11B R¹ is c-Pr 12B R¹ is n-Bu 13B R¹ is i-Bu 14B R¹ is n-pent 15B R¹ is n-Hex 16B R¹ is thp-4-yl 17B R¹ is thtp-4yl 18B R¹ is c-Hex 19B R¹ is CH₂CH₂OCH₃ 20B R¹ is CH₂CH₂OCH₂CH₃ 21B R¹ is CH₂CH₂CH₂OCH₃ 22B R¹ is CH₂CH₂CH₂OCH₂CH₃ 23B R¹ is Ph(3-OMe) 24B R¹ is Ph(4-OMe) 25B R¹ is Ph(3,4-di-OMe) 26B R¹ is Ph(2-F) 27B R¹ is Ph(3-F) 28B R¹ is Ph(4-F) 29B R¹ is Ph(3-Me) 30B R¹ is Ph(2-Me-3-F) 31B R¹ is Ph(2-Me-4-F) 32B R¹ is Ph(2-Me-5-F) 33B R¹ is Ph(2-F-3-Me) 34B R¹ is Ph(2-F-4-Me) 35B R¹ is Ph(2-F-5-Me) 36B R¹ is Ph(3-F-4-Me) 37B R¹ is Ph(3-F-5-Me) 38B R¹ is Ph(3-Me-4-F)

TABLE 3

R¹ is CH₃, R⁹ CH₃ R² R² Et Ph(2-Cl) n-Pr Ph(3-Cl) c-Pr Ph(4-Cl) CF₃ Ph(3-F) SMe Ph(3,5-di-F) Ph Ph(3-Me) The present disclosure also includes Tables 1C through 37C, each of which is constructed the same as Table 3 above except that the row heading in Table 3 (i.e. “R¹ is CH₃, R⁹ is CH₃”) is replaced with the respective row headings shown below. For example, in Table 1C the row heading is “R¹ is CH₂CH₃, R⁹ is CH₃”, and R² is as defined in Table 3 above. Thus, the first entry in Table 1C specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R¹ is CH₂CH₃; R² is Et; A is A-5; R³ is OH; R⁹ is CH₃; and R¹⁰ is H. Tables 2C through 27C are constructed similarly.

Table Row Heading  1C R¹ is CH₂CH₃, R⁹ is CH₃  2C R¹ is CH₂CH═CH₂, R⁹ is CH₃  3C R¹ is CH₂C≡CH, R⁹ is CH₃  4C R¹ is Ph, R⁹ is CH₃  5C R¹ is Ph(2-Me), R⁹ is CH₃  6C R¹ is Ph(4-Me), R⁹ is CH₃  7C R¹ is Ph(2-Me), R⁹ is CH₃  8C R¹ is Ph(3-Cl), R⁹ is CH₃  9C R¹ is CH₃, R⁹ is CH₂CH₃ 10C R¹ is CH₂CH₃, R⁹ is CH₂CH₃ 11C R¹ is CH₂CH═CH_(2,) R⁹ is CH₂CH₃ 12C R¹ is CH₂C≡CH, R⁹ is CH₂CH₃ 13C R¹ is Ph, R⁹ is CH₂CH₃ 14C R¹ is Ph(2-Me), R⁹ is CH₂CH₃ 15C R¹ is Ph(4-Me), R⁹ is CH₂CH₃ 16C R¹ is Ph(2-Cl), R⁹ is CH₂CH₃ 17C R¹ is Ph(3-Cl), R⁹ is CH₂CH₃ 18C R¹ is n-Bu, R⁹ is CH₃ 19C R¹ is n-pent, R⁹ is CH₃ 20C R¹ is n-Hex, R⁹ is CH₃ 21C R¹ is thp-4-yl, R⁹ is CH₃ 22C R¹ is thtp-4-yl, R⁹ is CH₃ 23C R¹ is c-Hex, R⁹ is CH₃ 24C R¹ is CH₂CH₂OCH₃, R⁹ is CH₃ 25C R¹ is CH₂CH₂OCH₂CH₃, R⁹ is CH₃ 26C R¹ is CH₂CH₂CH₂OCH₃, R⁹ is CH₃ 27C R¹ is CH₂CH₂CH₂OEt, R⁹ is CH₃ 28C R¹ is n-Bu, R⁹ is CH₂CH₃ 29C R¹ is n-pent, R⁹ is CH₂CH₃ 30C R¹ is n-Hex, R⁹ is CH₂CH₃ 31C R¹ is thp-4-yl, R⁹ is CH₂CH₃ 32C R¹ is thtp-4-yl, R⁹ is CH₂CH₃ 33C R¹ is c-Hex, R⁹ is CH₂CH₃ 34C R¹ is CH₂CH₂OCH₃, R⁹ is CH₂CH₃ 35C R¹ is CH₂CH₂OCH₂CH₃, R⁹ is CH₂CH₃ 36C R¹ is CH₂CH₂CH₂OCH₃, R⁹ is CH₂CH₃ 37C R¹ is CH₂CH₂CH₂OEt, R⁹ is CH₂CH₃

TABLE 4

R¹ is CH₃, R⁹ is CH₃ R² R² Et Ph(2-Cl) n-Pr Ph(3-Cl) c-Pr Ph(4-Cl) CF₃ Ph(3-F) SMe Ph(3,5-di-F) Ph Ph(3-Me) The present disclosure also includes Tables 1D through 37D, each of which is constructed the same as Table 4 above except that the row heading in Table 4 (i.e. “R¹ is CH₃, R⁹ is CH₃”) is replaced with the respective row headings shown below. For example, in Table 1D the row heading is “R¹ is CH₂CH₃, R⁹ is CH₃”, and R² is as defined in Table 4 above. Thus, the first entry in Table 1D specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R¹ is CH₂CH₃; R² is Et; A is A-5; R³ is OH; R⁹ is CH₃; and R¹⁰ is CH₃. Tables 2D through 37D are constructed similarly.

Table Row Heading  1D R¹ is CH₂CH₃, R⁹ is CH₃  2D R¹ is CH₂CH═CH₂, R⁹ is CH₃  3D R¹ is CH₂C≡CH, R⁹ is CH₃  4D R¹ is Ph, R⁹ is CH₃  5D R¹ is Ph(2-Me), R⁹ is CH₃  6D R¹ is Ph(4-Me), R⁹ is CH₃  7D R¹ is Ph(2-Me), R⁹ is CH₃ R⁵ is CH₃  8D R¹ is Ph(3-Cl), R⁹ is CH3  9D R¹ is CH₃, R⁹ is CH₂CH₃ 10D R¹ is CH₂CH₃, R⁹ is CH₂CH₃ 11D R¹ is CH₂CH═CH₂, R⁹ is CH₂CH₃ 12D R¹ is CH₂C≡CH, R⁹ is CH₂CH₃ 13D R¹ is Ph, R⁹ is CH₂CH₃ 14D R¹ is Ph(2-Me), R⁹ is CH₂CH₃ 15D R¹ is Ph(4-Me), R⁹ is CH₂CH₃ 16D R¹ is Ph(2-Cl), R⁹ is CH₂CH₃ 17D R¹ is Ph(3-Cl), R⁹ is CH₂CH₃ 18D R¹ is n-Bu, R⁹ is CH₃ 19D R¹ is n-pent, R⁹ is CH₃ 20D R¹ is n-Hex, R⁹ is CH₃ 21D R¹ is thp-4-yl, R⁹ is CH₃ 22D R¹ is thtp-4-yl, R⁹ is CH₃ 23D R¹ is c-Hex, R⁹ is CH₃ 24D R¹ is CH₂CH₂OCH₃, R⁹ is CH₃ 25D R¹ is CH₂CH₂OCH₂CH₃, R⁹ is CH₃ 26D R¹ is CH₂CH₂CH₂OCH₃, R⁹ is CH₃ 27D R¹ is CH₂CH₂CH₂OEt, R⁹ is CH₃ 28D R¹ is n-Bu, R⁹ is CH₂CH₃ 29D R¹ is n-pent, R⁹ is CH₂CH₃ 30D R¹ is n-Hex, R⁹ is CH₂CH₃ 31D R¹ is thp-4-yl, R⁹ is CH₂CH₃ 32D R¹ is thtp-4-yl, R⁹ is CH₂CH₃ 33D R¹ is c-Hex, R⁹ is CH₂CH₃ 34D R¹ is CH₂CH₂OCH₃, R⁹ is CH₂CH₃ 35D R¹ is CH₂CH₂OCH₂CH₃, R⁹ is CH₂CH₃ 36D R¹ is CH₂CH₂CH₂OCH₃, R⁹ is CH₂CH₃ 37D R¹ is CH₂CH₂CH₂OEt, R⁹ is CH₂CH₃

TABLE 5

R² is Ph R¹ R¹ Me Ph Et CH₂-c-Pr n-Pr CH₂-c-Bu i-Pr CH₂SPh c-Pr CH₂SCH₃ n-Bu CH₂CF₃ i-Bu CH₂Ph s-Bu Ph(4-Me) c-Bu CH₂CHC(CH₃)₂ t-Bu CH₂CH₂C≡CH n-pent CH₂CH═CCl₂ c-Pent CH₂CH═CF₂ n-Hex CH₂CF═CF₂ c-Hex CH₂CCl═CCl₂ CH₂C≡CCH₃ isoxazolin-2-yl CH₂OCH₂CH₃ Ph(2-Cl) CH₂CH₂OCH₃ Ph(3 -Cl) CH₂SO₂CH₃ Ph(4-Cl) CH₂SCH₂CH₃ Ph(2-Me) Ph(2,3-di-OMe) Ph(3-Me) CH₂SO₂-n-Pr CH₂OCH₃ CH₂CH₂SO₂Et CH₂CH═CH₂ Ph(2,4-di-OMe) Ph(2-OMe) Ph(2,5-di-OMe) Ph(3-OMe) Ph(2,6-di-OMe) Ph(4-OMe) Ph(3,5-di-OMe) Ph(2-CN) CH₂Ph(2-OMe) Ph(3-CN) CH₂Ph(3-OMe) Ph(4-CN) CH₂Ph(4-OMe) Ph(2-F) CH₂CH₂SMe Ph(3-F) CH₂SCH₂Ph Ph(4-F) CH₂SO₂Ph CH₂S-n-Pr CH₂CH₂SEt CH₂-c-Pent Ph(2,4-di-Cl) oxazolin-2-yl Ph(2,5-di-Cl) 2-pyridinyl Ph(2,6-di-Cl) 3-pyridinyl Ph(3,5-di-Cl) 4-pyridinyl Ph(2,3-di-Me) Ph(2-NO₂) Ph(2,4-di-Me) Ph(3-NO₂) Ph(2,5-di-Me) Ph(4-NO₂) Ph(2,6-di-Me) Ph(2-CF₃) Ph(3,5-di-Me) Ph(3-CF₃) CH₂-c-Hex Ph(4-CF₃) Ph(2,3-di-F) Ph(2-Br) Ph(2,4-di-F) Ph(3-Br) Ph(2,5-di-F) Ph(4-Br) Ph(2,6-di-F) CH₂Ph(2-Me) CH₂CH₂CF₃ CH₂Ph(3-Me) CH₂C≡CH CH₂Ph(4-Me) Ph(2,3-di-Cl) CH₂Ph(2-Cl) Ph(3,5-di-F) CH₂Ph(3-Cl) CH₂Ph(4-Cl) Ph(3,4-di-F) thiazol-3-yl Ph(3,4,5-tri-OMe) thiazol-2-yl Ph(2-I) thiazolin-2-yl Ph(3-I) thiazol-2-yl Ph(4-I) oxazol-2-yl Ph(2-Et) CH₂CF₂CF₃ Ph(3-Et) CH═CH₂ Ph(4-Et) CH₂(thf-2-yl) CH₂CH₂OCH₂CH₃ CH₂(3-methylisoxazolin-5-yl) CH(CH₃)CH₂OCH₃ isoxazolin-4-yl Ph(2-OCF₃) CH₂(3-methylisoxazol-5-yl) Ph(3-OCF₃) 5-methylisoxazol-3-yl Ph(4-OCF₃) 4-methyloxazol-2-yl Ph(2-Me-3-F) 4-methylthiazol-2-yl Ph(2-Me-4-F) CH₂CH₂CH═CH₂ Ph(2-Me-5-F) CH₂SO₂CH₂CH₃ Ph(2-F-3-Me) CH₂CH₂SO₂Me Ph(2-F-4-Me) CH₂OCH₂OCH₃ Ph(2-F-5-Me) 3-methylthiazol-2-yl Ph(3-F-4-Me) 5-chloropyridin-2-yl Ph(3-F-5-Me) 5-methylpyridin-2-yl Ph(3-Me-4-F) 5-methoxypyridin-2-yl CH₂CH₂CH₂OCH₃ 6-methylpyridin-2-yl CH₂CH₂CH₂OCH₂CH₃ 6-methylpyridin-3-yl CH₂(thp-2-yl) 3-methoxypyridin-4-yl CH₂(thp-4-yl) 3-methylpyridin-4-yl CH₂CH₂CH═CH₂ 3-chloropyridin-4-yl CH₂C≡CH CH₂OCH₂CH₂OCH₃ CH₂CH₂SCH₃ CH₂C(CH₃)C(CH₃)₂ CH₂CH₂SOCH₃ n-hept CH₂CH₂SO₂CH₃ c-hept CH₂CH₂CH₂SCH₃ thp-4-yl CH₂CH₂CH₂SOCH₃ thtp-4-yl CH₂CH₂CH₂SO₂CH₃ Ph(2,3-di-OMe) c-hex(3-OCH₃) Ph(3,4-di-OMe) c-hex(4-OCH₃) Ph(3,4-di-Me) c-hex(3,4-di-OCH₃) c-hex(3,5-di-OCH₃) CH₂CH₂SCH₃ The present disclosure also includes Tables 1E through 57E, each of which is constructed the same as Table 1 above except that the row heading in Table 1 (i.e. “R² is Ph”) is replaced with the respective row headings shown below. For example, in Table 1E the row heading is “R² is Me”, and R¹ is as defined in Table 5 above. Thus, the first entry in Table 1E specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R¹ is Me; R² is Me; R³ is OH; A is A-1; B¹ is C-1; B² is C-3; B³ is C-1; and each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is H. Tables 2E through 57E are constructed similarly.

Table Row Heading  1E R² is Me  2E R² is Et  3E R² is n-Pr  4E R² is c-Pr  5E R² is SMe  6E R² is SO₂Me  7E R² is CF₃  8E R² is Ph(2-Cl)  9E R² is Ph(3-Cl) 10E R² is Ph(4-Cl) 11E R² is Ph(2-Me) 12E R² is Ph(3-Me) 13E R² is Ph(4-Me) 14E R² is Ph(2-OMe) 15E R² is Ph(3-OMe) 16E R² is Ph(4-OMe) 17E R² is Ph(2-F) 18E R² is Ph(3-F) 19E R² is Ph(4-F) 20E R² is OMe 21E R² is OEt 22E R² is CH₂Ph 23E R² is 2-pyridinyl 24E R² is 3-pyridinyl 25E R² is 4-pyridinyl 26E R² is H 27E R² is Ph(3,5-di-F) 28E R² is Ph(3,4-di-F) 29E R² is Ph(3,4,5-tri-F) 30E R² is Ph(2,3-di-F) 31E R² is Ph(3-CF₃) 32E R² is Ph(4-CF₃) 33E R² is Ph(3,5-di-CF₃) 34E R² is n-Bu 35E R² is CH₂OCH₃ 36E R² is CH₂CH₂OCH₃ 37E R² is CH₂CH₂CF₃ 38E R² is CH₂CF₃ 39E R² is n-pent 40E R² is c-pent 41E R² is c-Hex 42E R² is n-Hex 43E R² is thp-4-yl 44E R² is Ph(2-CN) 45E R² is Ph(3-CN) 46E R² is Ph(4-CN) 47E R² is Ph(2-C≡CH) 48E R² is Ph(3-C≡CH) 49E R² is Ph(4-C≡CH) 50E R² is Ph(3-Me, 2-F) 51E R² is Ph(3-Me-4-F) 52E R² is Ph(3-Me, 5-F) 53E R² is Ph(3-Me, 6-F) 54E R² is Ph(3-F, 2-Me) 55E R² is Ph(3-F-4-Me) 56E R² is Ph(3-F-5-Me) 57E R² is Ph(3-F, 6-Me)

TABLE 6

R¹ is phenyl R² R³ Et OMe n-Pr OMe c-Pr OMe CF₃ OMe SMe OMe Ph OMe Ph(3-F) OMe Ph(3,5-di-F) OMe Ph(3-Me) OMe Et SPh n-Pr SPh c-Pr SPh CF₃ SPh SMe SPh Ph SPh Ph(3-F) SPh Ph(3,5-di-F) SPh Ph(3-Me) SPh Et OSO₂Ph n-Pr OSO₂Ph c-Pr OSO₂Ph CF₃ OSO₂Ph SMe OSO₂Ph Ph OSO₂Ph Ph(3-F) OSO₂Ph Ph(3,5-di-F) OSO₂Ph Ph(3-Me) OSO₂Ph Et OC(O)Ph n-Pr OC(O)Ph c-Pr OC(O)Ph CF₃ OC(O)Ph SMe OC(O)Ph Ph OC(O)Ph Et OC(O)Ph Ph(3-F) OC(O)Ph Ph(3,5-di-F) OC(O)Ph Ph(3-Me) OC(O)Ph n-Pr OC(O)CH₃ c-Pr OC(O)CH₃ CF₃ OC(O)CH₃ SMe OC(O)CH₃ Ph OC(O)CH₃ Ph(3-F) OC(O)CH₃ Ph(3,5-di-F) OC(O)CH₃ Ph(3-Me) OC(O)CH₃ The present disclosure also includes Tables 1F through 11F, each of which is constructed the same as Table 6 above except that the row heading in Table 6 (i.e. “R¹ is Ph”) is replaced with the respective row headings shown below. For example, in Table 1F the row heading is “R¹ is n-Pr”, and R² is as defined in Table 6 above. Thus, the first entry in Table 1F specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R¹ is phenyl; R² n-Pr; R³ is OMe; A is A-3; B² is C-3; T is —CH₂CH₂—; R¹⁸ and R¹⁹ are both H. Tables 2F through 11F are constructed similarly.

Table Row Heading  1F R¹ is n-Pr  2F R¹ is n-Bu  3F R¹ is n-pent  4F R¹ is n-Hex  5F R¹ is thp-4-yl  6F R¹ is thtp-4-yl  7F R¹ is c-Hex  8F R¹ is CH₂CH₂OCH₃  9F R¹ is CH₂CH₂OCH₂CH₃ 10F R¹ is CH₂CH₂CH₂OCH₃ 11F R¹ is CH₂CH₂CH₂OCH₂CH₃

TABLE 7

R² Et Ph(2-Me) n-Pr Ph(3-Cl) c-Pr Ph(4-Cl) CF₃ Ph(2-Me) SMe Ph(3-Me) Ph Ph(4-Me)

TABLE 8

R¹² is c-Pr R¹ R² CH₃ Et CH₃ n-Pr CH₃ c-Pr CH₃ CF₃ CH₃ SMe CH₃ Ph CH₃ Ph(2-Cl) CH₃ Ph(3-Cl) CH₃ Ph(4-Cl) CH₃ Ph(3-F) CH₃ Ph(3,5-di-F) CH₃ Ph(3-Me) Et Et Et n-Pr Et c-Pr Et CF₃ Et SMe Et Ph Et Ph(2-Cl) Et Ph(3-Cl) Et Ph(4-Cl) Et Ph(3-F) Et Ph(3,5-di-F) Et Ph(3-Me) CH₂CH═CH₂ Et CH₂CH═CH₂ n-Pr CH₂CH═CH₂ c-Pr CH₂CH═CH₂ CF₃ CH₂CH═CH₂ SMe CH₂CH═CH₂ Ph CH₂CH═CH₂ Ph(2-Cl) CH₂CH═CH₂ Ph(3-Cl) CH₂CH═CH₂ Ph(4-Cl) CH₂CH═CH₂ Ph(3-F) CH₂CH═CH₂ Ph(3,5-di-F) CH₂CH═CH₂ Ph(3-Me) CH₂C≡CH Et CH₂C≡CH n-Pr CH₂C≡CH c-Pr CH₂C≡CH CF₃ CH₂C≡CH SMe CH₂C≡CH Ph CH₂C≡CH Ph(2-Cl) CH₂C≡CH Ph(3-Cl) CH₂C≡CH Ph(4-Cl) CH₂C≡CH Ph(3-F) CH₂C≡CH Ph(3,5-di-F) CH₂C≡CH Ph(3-Me) Ph Et Ph n-Pr Ph c-Pr Ph CF₃ Ph SMe Ph Ph Ph Ph(2-Cl) Ph Ph(3-Cl) Ph Ph(4-Cl) Ph Ph(3-F) Ph Ph(3,5-di-F) Ph Ph(3-Me) Ph(2-Me) Et Ph(2-Me) n-Pr Ph(2-Me) c-Pr Ph(2-Me) CF₃ Ph(2-Me) SMe Ph(2-Me) Ph Ph(2-Me) Ph(2-Cl) Ph(2-Me) Ph(3-Cl) Ph(2-Me) Ph(4-Cl) Ph(2-Me) Ph(3-F) Ph(2-Me) Ph(3,5-di-F) Ph(2-Me) Ph(3-Me) Ph(4-Me) Et Ph(4-Me) n-Pr Ph(4-Me) c-Pr Ph(4-Me) CF₃ Ph(4-Me) SMe Ph(4-Me) Ph Ph(4-Me) Ph(2-Cl) Ph(4-Me) Ph(3-Cl) Ph(4-Me) Ph(4-Cl) Ph(4-Me) Ph(3-F) Ph(4-Me) Ph(3,5-di-F) Ph(4-Me) Ph(3-Me) Ph(2-Cl) Et Ph(2-Cl) n-Pr Ph(2-Cl) c-Pr Ph(2-Cl) CF₃ Ph(2-Cl) SMe Ph(2-Cl) Ph Ph(2-Cl) Ph(2-Cl) Ph(2-Cl) Ph(3-Cl) Ph(2-Cl) Ph(4-Cl) Ph(2-Cl) Ph(3-F) Ph(2-Cl) Ph(3,5-di-F) Ph(2-Cl) Ph(3-Me) Ph(3-Cl) Et Ph(3-Cl) n-Pr Ph(3-Cl) c-Pr Ph(3-Cl) CF₃ Ph(3-Cl) SMe Ph(3-Cl) Ph Ph(3-Cl) Ph(2-Cl) Ph(3-Cl) Ph(3-Cl) Ph(3-Cl) Ph(4-Cl) Ph(3-Cl) Ph(3-F) Ph(3-Cl) Ph(3,5-di-F) Ph(3-Cl) Ph(3-Me) n-Pr Et n-Pr n-Pr n-Pr c-Pr n-Pr CF₃ n-Pr SMe n-Pr Ph n-Pr Ph(2-Cl) n-Pr Ph(3-Cl) n-Pr Ph(4-Cl) n-Pr Ph(3-F) n-Pr Ph(3,5-di-F) n-Pr Ph(3-Me) c-Pr Et c-Pr n-Pr c-Pr c-Pr c-Pr CF₃ c-Pr SMe c-Pr Ph c-Pr Ph(2-Cl) c-Pr Ph(3-Cl) c-Pr Ph(4-Cl) c-Pr Ph(3-F) c-Pr Ph(3,5-di-F) c-Pr Ph(3-Me) n-Bu Et n-Bu n-Pr n-Bu c-Pr n-Bu CF₃ n-Bu SMe n-Bu Ph n-Bu Ph(2-Cl) n-Bu Ph(3-Cl) n-Bu Ph(4-Cl) n-Bu Ph(3-F) n-Bu Ph(3,5-di-F) n-Bu Ph(3-Me) n-pent Et n-pent n-Pr n-pent c-Pr n-pent CF₃ n-pent SMe n-pent Ph n-pent Ph(2-Cl) n-pent Ph(3-Cl) n-pent Ph(4-Cl) n-pent Ph(3-F) n-pent Ph(3,5-di-F) n-pent Ph(3-Me) n-Hex Et n-Hex n-Pr n-Hex c-Pr n-Hex CF₃ n-Hex SMe n-Hex Ph n-Hex Ph(2-Cl) n-Hex Ph(3-Cl) n-Hex Ph(4-Cl) n-Hex Ph(3-F) n-Hex Ph(3,5-di-F) n-Hex Ph(3-Me) thp-4-yl Et thp-4-yl n-Pr thp-4-yl c-Pr thp-4-yl CF₃ thp-4-yl SMe thp-4-yl Ph thp-4-yl Ph(2-Cl) thp-4-yl Ph(3-Cl) thp-4-yl Ph(4-Cl) thp-4-yl Ph(3-F) thp-4-yl Ph(3,5-di-F) thp-4-yl Ph(3-Me) c-Hex Et c-Hex n-Pr c-Hex c-Pr c-Hex CF₃ c-Hex SMe c-Hex Ph c-Hex Ph(2-Cl) c-Hex Ph(3-Cl) c-Hex Ph(4-Cl) c-Hex Ph(3-F) c-Hex Ph(3,5-di-F) c-Hex Ph(3-Me) CH₂CH₂OCH₃ Et CH₂CH₂OCH₃ n-Pr CH₂CH₂OCH₃ c-Pr CH₂CH₂OCH₃ CF₃ CH₂CH₂OCH₃ SMe CH₂CH₂OCH₃ Ph CH₂CH₂OCH₃ Ph(2-Cl) CH₂CH₂OCH₃ Ph(3-Cl) CH₂CH₂OCH₃ Ph(4-Cl) CH₂CH₂OCH₃ Ph(3-F) CH₂CH₂OCH₃ Ph(3,5-di-F) CH₂CH₂OCH₃ Ph(3-Me) CH₂CH₂OCH₂CH₃ Et CH₂CH₂OCH₂CH₃ n-Pr CH₂CH₂OCH₂CH₃ c-Pr CH₂CH₂OCH₂CH₃ CF₃ CH₂CH₂OCH₂CH₃ SMe CH₂CH₂OCH₂CH₃ Ph CH₂CH₂OCH₂CH₃ Ph(2-Cl) CH₂CH₂OCH₂CH₃ Ph(3-Cl) CH₂CH₂OCH₂CH₃ Ph(4-Cl) CH₂CH₂OCH₂CH₃ Ph(3-F) CH₂CH₂OCH₂CH₃ Ph(3,5-di-F) CH₂CH₂OCH₂CH₃ Ph(3-Me) CH₂CH₂CH₂OCH₃ Et CH₂CH₂CH₂OCH₃ n-Pr CH₂CH₂CH₂OCH₃ c-Pr CH₂CH₂CH₂OCH₃ CF₃ CH₂CH₂CH₂OCH₃ SMe CH₂CH₂CH₂OCH₃ Ph CH₂CH₂CH₂OCH₃ Ph(2-Cl) CH₂CH₂CH₂OCH₃ Ph(3-Cl) CH₂CH₂CH₂OCH₃ Ph(4-Cl) CH₂CH₂CH₂OCH₃ Ph(3-F) CH₂CH₂CH₂OCH₃ Ph(3,5-di-F) CH₂CH₂CH₂OCH₃ Ph(3-Me) CH₂CH₂CH₂OEt Et CH₂CH₂CH₂OEt n-Pr CH₂CH₂CH₂OEt c-Pr CH₂CH₂CH₂OEt CF₃ CH₂CH₂CH₂OEt SMe CH₂CH₂CH₂OEt Ph CH₂CH₂CH₂OEt Ph(2-Cl) CH₂CH₂CH₂OEt Ph(3-Cl) CH₂CH₂CH₂OEt Ph(4-Cl) CH₂CH₂CH₂OEt Ph(3-F) CH₂CH₂CH₂OEt Ph(3,5-di-F) CH₂CH₂CH₂OEt Ph(3-Me) The present disclosure also includes Tables 1H through 2H, each of which is constructed the same as Table 8 above except that the row heading in Table 8 (i.e. “R¹² is c-Pr”) is replaced with the respective row headings shown below. For example, in Table 1H the row heading is “R¹² is CH₃”, and R¹ and R² are as defined in Table 8 above. Thus, the first entry in Table 1H specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R¹ is CH₃; R² is Et; A is A-6; R¹¹ is H; and R¹² is CH₃. Table 2H is constructed similarly.

Table Row Heading 1H R¹² is CH₃ 2H R¹² is CH₂CH₃

TABLE 9

R¹² is c-Pr R¹ R² CH₃ Et CH₃ n-Pr CH₃ c-Pr CH₃ CF₃ CH₃ SMe CH₃ Ph CH₃ Ph(2-Cl) CH₃ Ph(3-Cl) CH₃ Ph(4-Cl) CH₃ Ph(3-F) CH₃ Ph(3,5-di-F) CH₃ Ph(3-Me) Et Et Et n-Pr Et c-Pr Et CF₃ Et SMe Et Ph Et Ph(2-Cl) Et Ph(3-Cl) Et Ph(4-Cl) Et Ph(3-F) Et Ph(3,5-di-F) Et Ph(3-Me) CH₂CH═CH₂ Et CH₂CH═CH₂ n-Pr CH₂CH═CH₂ c-Pr CH₂CH═CH₂ CF₃ CH₂CH═CH₂ SMe CH₂CH═CH₂ Ph CH₂CH═CH₂ Ph(2-Cl) CH₂CH═CH₂ Ph(3-Cl) CH₂CH═CH₂ Ph(4-Cl) CH₂CH═CH₂ Ph(3-F) CH₂CH═CH₂ Ph(3,5-di-F) CH₂CH═CH₂ Ph(3-Me) CH₂C≡CH Et CH₂C≡CH n-Pr CH₂C≡CH c-Pr CH₂C≡CH CF₃ CH₂C≡CH SMe CH₂C≡CH Ph CH₂C≡CH Ph(2-Cl) CH₂C≡CH Ph(3-Cl) CH₂C≡CH Ph(4-Cl) CH₂C≡CH Ph(3-F) CH₂C≡CH Ph(3,5-di-F) CH₂C≡CH Ph(3-Me) Ph Et Ph n-Pr Ph c-Pr Ph CF₃ Ph SMe Ph Ph Ph Ph(2-Cl) Ph Ph(3-Cl) Ph Ph(4-Cl) Ph Ph(3-F) Ph Ph(3,5-di-F) Ph Ph(3-Me) Ph(2-Me) Et Ph(2-Me) n-Pr Ph(2-Me) c-Pr Ph(2-Me) CF₃ Ph(2-Me) SMe Ph(2-Me) Ph Ph(2-Me) Ph(2-Cl) Ph(2-Me) Ph(3-Cl) Ph(2-Me) Ph(4-Cl) Ph(2-Me) Ph(3-F) Ph(2-Me) Ph(3,5-di-F) Ph(2-Me) Ph(3-Me) Ph(4-Me) Et Ph(4-Me) n-Pr Ph(4-Me) c-Pr Ph(4-Me) CF₃ Ph(4-Me) SMe Ph(4-Me) Ph Ph(4-Me) Ph(2-Cl) Ph(4-Me) Ph(3-Cl) Ph(4-Me) Ph(4-Cl) Ph(4-Me) Ph(3-F) Ph(4-Me) Ph(3,5-di-F) Ph(4-Me) Ph(3-Me) Ph(2-Cl) Et Ph(2-Cl) n-Pr Ph(2-Cl) c-Pr Ph(2-Cl) CF₃ Ph(2-Cl) SMe Ph(2-Cl) Ph Ph(2-Cl) Ph(2-Cl) Ph(2-Cl) Ph(3-Cl) Ph(2-Cl) Ph(4-Cl) Ph(2-Cl) Ph(3-F) Ph(2-Cl) Ph(3,5-di-F) Ph(2-Cl) Ph(3-Me) Ph(3-Cl) Et Ph(3-Cl) n-Pr Ph(3-Cl) c-Pr Ph(3-Cl) CF₃ Ph(3-Cl) SMe Ph(3-Cl) Ph Ph(3-Cl) Ph(2-Cl) Ph(3-Cl) Ph(3-Cl) Ph(3-Cl) Ph(4-Cl) Ph(3-Cl) Ph(3-F) Ph(3-Cl) Ph(3,5-di-F) Ph(3-Cl) Ph(3-Me) n-Pr Et n-Pr n-Pr n-Pr c-Pr n-Pr CF₃ n-Pr SMe n-Pr Ph n-Pr Ph(2-Cl) n-Pr Ph(3-Cl) n-Pr Ph(4-Cl) n-Pr Ph(3-F) n-Pr Ph(3,5-di-F) n-Pr Ph(3-Me) n-Bu Et n-Bu n-Pr n-Bu c-Pr n-Bu CF₃ n-Bu SMe n-Bu Ph n-Bu Ph(2-Cl) n-Bu Ph(3-Cl) n-Bu Ph(4-Cl) n-Bu Ph(3-F) n-Bu Ph(3,5-di-F) n-Bu Ph(3-Me) n-pent Et n-pent n-Pr n-pent c-Pr n-pent CF₃ n-pent SMe n-pent Ph n-pent Ph(2-Cl) n-pent Ph(3-Cl) n-pent Ph(4-Cl) n-pent Ph(3-F) n-pent Ph(3,5-di-F) n-pent Ph(3-Me) n-Hex Et n-Hex n-Pr n-Hex c-Pr n-Hex CF₃ n-Hex SMe n-Hex Ph n-Hex Ph(2-Cl) n-Hex Ph(3-Cl) n-Hex Ph(4-Cl) n-Hex Ph(3-F) n-Hex Ph(3,5-di-F) n-Hex Ph(3-Me) thp-4-yl Et thp-4-yl n-Pr thp-4-yl c-Pr thp-4-yl CF₃ thp-4-yl SMe thp-4-yl Ph thp-4-yl Ph(2-Cl) thp-4-yl Ph(3-Cl) thp-4-yl Ph(4-Cl) thp-4-yl Ph(3-F) thp-4-yl Ph(3,5-di-F) thp-4-yl Ph(3-Me) thtp-4-yl Et thtp-4-yl n-Pr thtp-4-yl c-Pr thtp-4-yl CF₃ thtp-4-yl SMe thtp-4-yl Ph thtp-4-yl Ph(2-Cl) thtp-4-yl Ph(3-Cl) thtp-4-yl Ph(4-Cl) thtp-4-yl Ph(3-F) thtp-4-yl Ph(3,5-di-F) thtp-4-yl Ph(3-Me) c-Hex Et c-Hex n-Pr c-Hex c-Pr c-Hex CF₃ c-Hex SMe c-Hex Ph c-Hex Ph(2-Cl) c-Hex Ph(3-Cl) c-Hex Ph(4-Cl) c-Hex Ph(3-F) c-Hex Ph(3,5-di-F) c-Hex Ph(3-Me) CH₂CH₂OCH₃ Et CH₂CH₂OCH₃ n-Pr CH₂CH₂OCH₃ c-Pr CH₂CH₂OCH₃ CF₃ CH₂CH₂OCH₃ SMe CH₂CH₂OCH₃ Ph CH₂CH₂OCH₃ Ph(2-Cl) CH₂CH₂OCH₃ Ph(3-Cl) CH₂CH₂OCH₃ Ph(4-Cl) CH₂CH₂OCH₃ Ph(3-F) CH₂CH₂OCH₃ Ph(3,5-di-F) CH₂CH₂OCH₃ Ph(3-Me) CH₂CH₂OCH₂CH₃ Et CH₂CH₂OCH₂CH₃ n-Pr CH₂CH₂OCH₂CH₃ c-Pr CH₂CH₂OCH₂CH₃ CF₃ CH₂CH₂OCH₂CH₃ SMe CH₂CH₂OCH₂CH₃ Ph CH₂CH₂OCH₂CH₃ Ph(2-Cl) CH₂CH₂OCH₂CH₃ Ph(3-Cl) CH₂CH₂OCH₂CH₃ Ph(4-Cl) CH₂CH₂OCH₂CH₃ Ph(3-F) CH₂CH₂OCH₂CH₃ Ph(3,5-di-F) CH₂CH₂OCH₂CH₃ Ph(3-Me) CH₂CH₂CH₂OCH₃ Et CH₂CH₂CH₂OCH₃ n-Pr CH₂CH₂CH₂OCH₃ c-Pr CH₂CH₂CH₂OCH₃ CF₃ CH₂CH₂CH₂OCH₃ SMe CH₂CH₂CH₂OCH₃ Ph CH₂CH₂CH₂OCH₃ Ph(2-Cl) CH₂CH₂CH₂OCH₃ Ph(3-Cl) CH₂CH₂CH₂OCH₃ Ph(4-Cl) CH₂CH₂CH₂OCH₃ Ph(3-F) CH₂CH₂CH₂OCH₃ Ph(3,5-di-F) CH₂CH₂CH₂OCH₃ Ph(3-Me) CH₂CH₂CH₂OEt Et CH₂CH₂CH₂OEt n-Pr CH₂CH₂CH₂OEt c-Pr CH₂CH₂CH₂OEt CF₃ CH₂CH₂CH₂OEt SMe CH₂CH₂CH₂OEt Ph CH₂CH₂CH₂OEt Ph(2-Cl) CH₂CH₂CH₂OEt Ph(3-Cl) CH₂CH₂CH₂OEt Ph(4-Cl) CH₂CH₂CH₂OEt Ph(3-F) CH₂CH₂CH₂OEt Ph(3,5-di-F) CH₂CH₂CH₂OEt Ph(3-Me) The present disclosure also includes Tables 1J through 2J, each of which is constructed the same as Table 9 above except that the row heading in Table 9 (i.e. “R¹² is c-Pr”) is replaced with the respective row headings shown below. For example, in Table 1J the row heading is “R¹² is CH₃”, and R¹ and R² are as defined in Table 9 above. Thus, the first entry in Table 1J specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R¹ is CH₃; R² is Et; A is A-7; R¹² is CH₃; and R¹³ is cyano. Table 2J is constructed similarly.

Table Row Heading 1J R¹² is CH₃ 2J R¹² is CH₂CH₃

TABLE 10

R¹ is phenyl R² Et Ph(2-Me) n-Pr Ph(3-Cl) c-Pr Ph(4-Cl) CF₃ Ph(2-Me) SMe Ph(3-Me) Ph Ph(4-Me) Ph(3-F) Ph(3,5-di-F) Ph(3-Me) The present disclosure also includes Tables 1K through 10K, each of which is constructed the same as Table 9 above except that the row heading in Table 10 (i.e. “R¹ is Ph”) is replaced with the respective row headings shown below. For example, in Table 1K the row heading is “R¹ is n-Bu”, and R² is as defined in Table 10 above. Thus, the first entry in Table 1K specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R¹ is n-Bu; R² is Ph; A is A-7; R¹² is hydroxy; and R¹³ is nitro. Table 2K through 10K are constructed similarly.

Table Row Heading  1K R¹ is n-Bu  2K R¹ is n-pent  3K R¹ is n-Hex  4K R¹ is thp-4-yl  5K R¹ is thtp-4-yl  6K R¹ is c-Hex  7K R¹ is CH₂CH₂OCH₃  8K R¹ is CH₂CH₂OCH₂CH₃  9K R¹ is CH₂CH₂CH₂OCH₃ 10K R¹ is CH₂CH₂CH₂OCH₂CH₃

TABLE 11

R²⁴ Q is CH₂ H Ph Et Ph(3-Cl) n-Pr Ph(3-F) OCH₂CH₂OCH₃ Ph(3-OMe) Ph(4-OMe) Ph(3,5-di-F) Q is —CH₂CH₂— H Ph Et Ph(3-Cl) n-Pr Ph(3-F) OCH₂CH₂OCH₃ Ph(3-OMe) Ph(4-OMe) Ph(3,5-di-F) Q is O H Ph Et Ph(3-Cl) n-Pr Ph(3-F) OCH₂CH₂OCH₃ Ph(3-OMe) Ph(4-OMe) Ph(3,5-di-F) Q is NCH₃ H Ph Et Ph(3-Cl) n-Pr Ph(3-F) OCH₂CH₂OCH₃ Ph(3-OMe) Ph(4-OMe) Ph(3,5-di-F) Q is S H Ph Et Ph(3-Cl) n-Pr Ph(3-F) OCH₂CH₂OCH₃ Ph(3-OMe) Ph(4-OMe) Ph(3,5-di-F) Q is S(O) H Ph Et Ph(3-Cl) n-Pr Ph(3-F) OCH₂CH₂OCH₃ Ph(3-OMe) Ph(4-OMe) Ph(3,5-di-F) Q is S(O)₂ H Ph Et Ph(3-Cl) n-Pr Ph(3-F) OCH₂CH₂OCH₃ Ph(3-OMe) Ph(4-OMe) Ph(3,5-di-F)

TABLE 12 Table 12 is constructed the same as Table 11, except the structure is replaced with

TABLE 13

R²⁴ Q is O H Ph Et Ph(3-Cl) n-Pr Ph(3-F) OCH₂CH₂OCH₃ Ph(3-OMe) Ph(4-OMe) Ph(3,5-di-F) Q is NCH₃ H Ph Et Ph(3-Cl) n-Pr Ph(3-F) OCH₂CH₂OCH₃ Ph(3-OMe) Ph(4-OMe) Ph(3,5-di-F) Q is S H Ph Et Ph(3-Cl) n-Pr Ph(3-F) OCH₂CH₂OCH₃ Ph(3-OMe) Ph(4-OMe) Ph(3,5-di-F) Q is S(O) H Ph Et Ph(3-Cl) n-Pr Ph(3-F) OCH₂CH₂OCH₃ Ph(3-OMe) Ph(4-OMe) Ph(3,5-di-F) Q is S(O)₂ H Ph Et Ph(3-Cl) n-Pr Ph(3-F) OCH₂CH₂OCH₃ Ph(3-OMe) Ph(4-OMe) Ph(3,5-di-F)

TABLE 14 Table 14 is constructed the same as Table 13, except the structure is replaced with

TABLE 15 Table 15 is constructed the same as Table 13, except the structure is replaced with

TABLE 16 Table 16 is constructed the same as Table 13, except the structure is replaced with

TABLE 17 Table 17 is constructed the same as Table 13, except the structure is replaced with

TABLE 18 Table 18 is constructed the same as Table 13, except the structure is replaced with

TABLE 19

R² is Ph R¹ Me Et n-Pr i-Pr c-Pr n-Bu i-Bu s-Bu c-Bu t-Bu n-pent c-Pent n-Hex c-Hex Ph CH₂-c-Pr CH₂-c-Bu CH₂SPh CH₂SCH₃ CH₂CF₃ CH₂Ph Ph(4-Me) CH₂CHC(CH₃)₂ CH₂CH₂C≡CH CH₂CH═CCl₂ CH₂CH═CF₂ CH₂CF═CF₂ CH₂CCl═CCl₂ CH₂C≡CCH₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ CH₂SO₂CH₃ CH₂SCH₂CH₃ Ph(2,3-di-OMe) CH₂SO₂-n-Pr CH₂CH₂SO₂Et Ph(2,4-di-OMe) Ph(2,5-di-OMe) Ph(2,6-di-OMe) Ph(3,5-di-OMe) CH₂Ph(2-OMe) CH₂Ph(3-OMe) CH₂Ph(4-OMe) CH₂CH₂SMe CH₂SCH₂Ph CH₂SO₂Ph CH₂CH₂SEt Ph(2,4-di-Cl) Ph(2,5-di-Cl) Ph(2,6-di-Cl) Ph(3,5-di-Cl) Ph(2,3-di-Me) Ph(2,4-di-Me) Ph(2,5-di-Me) Ph(2,6-di-Me) Ph(3,5-di-Me) CH₂-c-Hex Ph(2,3-di-F) Ph(2,4-di-F) Ph(2,5-di-F) Ph(2,6-di-F) CH₂CH₂CF₃ CH₂C≡CH Ph(2,3-di-Cl) Ph(3,5-di-F) isoxazolin-2-yl Ph(2-Cl) Ph(3-Cl) Ph(4-Cl) Ph(2-Me) Ph(3-Me) CH₂OCH₃ CH₂CH═CH₂ Ph(2-OMe) Ph(3-OMe) Ph(4-OMe) Ph(2-CN) Ph(3-CN) Ph(4-CN) Ph(2-F) Ph(3-F) Ph(4-F) CH₂S-n-Pr CH₂-c-Pent oxazolin-2-yl 2-pyridinyl 3-pyridinyl 4-pyridinyl Ph(2-NO₂) Ph(3-NO₂) Ph(4-NO₂) Ph(2-CF₃) Ph(3-CF₃) Ph(4-CF₃) Ph(2-Br) Ph(3-Br) Ph(4-Br) CH₂Ph(2-Me) CH₂Ph(3-Me) CH₂Ph(4-Me) CH₂Ph(2-Cl) CH₂Ph(3-Cl) CH₂Ph(4-Cl) thiazol-3-yl thiazol-2-yl thiazolin-2-yl thiazol-2-yl oxazol-2-yl CH₂CF₂CF₃ CH═CH₂ CH₂(thf-2-yl) CH₂(3-methylisoxazolin-5-yl) isoxazolin-4-yl CH₂(3-methylisoxazol-5-yl) 5-methylisoxazol-3-yl 4-methyloxazol-2-yl 4-methylthiazol-2-yl CH₂CH₂CH═CH₂ CH₂SO₂CH₂CH₃ CH₂CH₂SO₂Me CH₂OCH₂OCH₃ 3-methylthiazol-2-yl 5-chloropyridin-2-yl 5-methylpyridin-2-yl 5-methoxypyridin-2-yl 6-methylpyridin-2-yl 6-methylpyridin-3-yl 3-methoxypyridin-4-yl 3-methylpyridin-4-yl 3-chloropyridin-4-yl CH₂OCH₂CH₂OCH₃ CH₂C(CH₃)C(CH₃)₂ n-hept c-hept thp-4-yl thtp-4-yl Ph(2,3-di-OMe) Ph(3,4-di-OMe) Ph(3,4-di-Me) Ph(3,4-di-F) Ph(3,4,5-tri-OMe) Ph(2-I) Ph(3-I) Ph(4-I) Ph(2-Et) Ph(3-Et) Ph(4-Et) CH₂CH₂OCH₂CH₃ CH(CH₃)CH₂OCH₃ Ph(2-OCF₃) Ph(3-OCF₃) Ph(4-OCF₃) Ph(2-Me-3-F) Ph(2-Me-4-F) Ph(2-Me-5-F) Ph(2-F-3-Me) Ph(2-F-4-Me) Ph(2-F-5-Me) Ph(3-F-4-Me) Ph(3-F-5-Me) Ph(3-Me-4-F) CH₂CH₂CH₂OCH₃ CH₂CH₂CH₂OCH₂CH₃ CH2(thp-2-yl) CH2(thp-4-yl) CH₂CH₂CH═CH₂ CH₂C≡CH CH₂CH₂SCH₃ CH₂CH₂SOCH₃ CH₂CH₂SO₂CH₃ CH₂CH₂CH₂SCH₃ CH₂CH₂CH₂SOCH₃ CH₂CH₂CH₂SO₂CH₃ The present disclosure also includes Tables 1U through 57U, each of which is constructed the same as Table 19 above except that the row heading in Table 19 (i.e. “R² is Ph”) is replaced with the respective row headings shown below. For example, in Table 1U the row heading is “R² is Me”, and R¹ is as defined in Table 19 above. Thus, the first entry in Table 1U specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R¹ is Me; R² is Me; R³ is OH; A is A-1; B¹ is C-1; B² is C-3; B³ is C-1; and each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is H. Tables 2U through 57U are constructed similarly.

Table Row Heading  1U R² is Me  2U R² is Et  3U R² is n-Pr  4U R² is c-Pr  5U R² is SMe  6U R² is SO₂Me  7U R² is CF₃  8U R² is Ph(2-Cl)  9U R² is Ph(3-Cl) 10U R² is Ph(4-Cl) 11U R² is Ph(2-Me) 12U R² is Ph(3-Me) 13U R² is Ph(4-Me) 14U R² is Ph(2-OMe) 15U R² is Ph(3-OMe) 16U R² is Ph(4-OMe) 17U R² is Ph(2-F) 18U R² is Ph(3-F) 19U R² is Ph(4-F) 20U R² is OMe 21U R² is OEt 22U R² is CH₂Ph 23U R² is 2-pyridinyl 24U R² is 3-pyridinyl 25U R² is 4-pyridinyl 26U R² is H 27U R² is Ph(3,5-di-F) 28U R² is Ph(3,4-di-F) 29U R² is Ph(3,4,5-tri-F) 30U R² is Ph(2,3-di-F) 31U R² is Ph(3-CF₃) 32U R² is Ph(4-CF₃) 33U R² is Ph(3,5-di-CF₃) 34U R² is n-Bu 35U R² is CH₂OCH₃ 36U R² is CH₂CH₂OCH₃ 37U R² is CH₂CH₂CF₃ 38U R² is CH₂CF₃ 39U R² is n-pent 40U R² is c-pent 41U R² is c-Hex 42U R² is n-Hex 43U R² is thp-4-yl 44U R² is Ph(2-CN) 45U R² is Ph(3-CN) 46U R² is Ph(4-CN) 47U R² is Ph(2-C≡CH) 48U R² is Ph(3-C≡CH) 49U R² is Ph(4-C≡CH) 50U R² is Ph(3-Me, 2-F) 51U R² is Ph(3-Me-4-F) 52U R² is Ph(3-Me, 5-F) 53U R² is Ph(3-Me, 6-F) 54U R² is Ph(3-F, 2-Me) 55U R² is Ph(3-F-4-Me) 56U R² is Ph(3-F-5-Me) 57U R² is Ph(3-F, 6-Me)

TABLE 20 Table 20 is constructed the same as Table 19 except the structure is replaced with

TABLE 21 Table 21 is constructed the same as Table 19 except the structure is replaced with

TABLE 22 Table 22 is constructed the same as Table 19 except the structure is replaced with

TABLE 23 Table 23 is constructed the same as Table 19 except the structure is replaced with

TABLE 24 Table 24 is constructed the same as Table 19 except the structure is replaced with

TABLE 25 Table 25 is constructed the same as Table 19 except the structure is replaced with

TABLE 26 Table 26 is the same as Table19 except the structure is replaced with

TABLE 27

R² is Ph R¹ Me Et n-Pr i-Pr c-Pr n-Bu i-Bu s-Bu c-Bu t-Bu n-pent c-Pent n-Hex c-Hex Ph CH₂-c-Pr CH₂-c-Bu CH₂SPh CH₂SCH₃ CH₂CF₃ CH₂Ph Ph(4-Me) CH₂CHC(CH₃)₂ CH₂CH₂C≡CH CH₂CH═CCl₂ CH₂CH═CF₂ CH₂CF═CF₂ CH₂CCl═CCl₂ CH₂C≡CCH₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ CH₂SO₂CH₃ CH₂SCH₂CH₃ Ph(2,3-di-OMe) CH₂SO₂-n-Pr CH₂CH₂SO₂Et Ph(2,4-di-OMe) Ph(2,5-di-OMe) Ph(2,6-di-OMe) Ph(3,5-di-OMe) CH₂Ph(2-OMe) CH₂Ph(3-OMe) CH₂Ph(4-OMe) CH₂CH₂SMe CH₂SCH₂Ph CH₂SO₂Ph CH₂CH₂SEt Ph(2,4-di-Cl) Ph(2,5-di-Cl) Ph(2,6-di-Cl) Ph(3,5-di-Cl) Ph(2,3-di-Me) Ph(2,4-di-Me) Ph(2,5-di-Me) Ph(2,6-di-Me) Ph(3,5-di-Me) CH₂-c-Hex Ph(2,3-di-F) Ph(2,4-di-F) Ph(2,5-di-F) Ph(2,6-di-F) CH₂CH₂CF₃ CH₂C≡CH Ph(2,3-di-Cl) Ph(3,5-di-F) isoxazolin-2-yl Ph(2-Cl) Ph(3-Cl) Ph(4-Cl) Ph(2-Me) Ph(3-Me) CH₂OCH₃ CH₂CH═CH₂ Ph(2-OMe) Ph(3-OMe) Ph(4-OMe) Ph(2-CN) Ph(3-CN) Ph(4-CN) Ph(2-F) Ph(3-F) Ph(4-F) CH₂S-n-Pr CH₂-c-Pent oxazolin-2-yl 2-pyridinyl 3-pyridinyl 4-pyridinyl Ph(2-NO₂) Ph(3-NO₂) Ph(4-NO₂) Ph(2-CF₃) Ph(3-CF₃) Ph(4-CF₃) Ph(2-Br) Ph(3-Br) Ph(4-Br) CH₂Ph(2-Me) CH₂Ph(3-Me) CH₂Ph(4-Me) CH₂Ph(2-Cl) CH₂Ph(3-Cl) CH₂Ph(4-Cl) thiazol-3-yl thiazol-2-yl thiazolin-2-yl thiazol-2-yl oxazol-2-yl CH₂CF₂CF₃ CH═CH₂ CH₂(thf-2-yl) CH₂(3-methylisoxazolin-5-yl) isoxazolin-4-yl CH₂(3-methylisoxazol-5-yl) 5-methylisoxazol-3-yl 4-methyloxazol-2-yl 4-methylthiazol-2-yl CH₂CH₂CH═CH₂ CH₂SO₂CH₂CH₃ CH₂CH₂SO₂Me CH₂OCH₂OCH₃ 3-methylthiazol-2-yl 5-chloropyridin-2-yl 5-methylpyridin-2-yl 5-methoxypyridin-2-yl 6-methylpyridin-2-yl 6-methylpyridin-3-yl 3-methoxypyridin-4-yl 3-methylpyridin-4-yl 3-chloropyridin-4-yl CH₂OCH₂CH₂OCH₃ CH₂C(CH₃)C(CH₃)₂ n-hept c-hept thp-4-yl thtp-4-yl Ph(2,3-di-OMe) Ph(3,4-di-OMe) Ph(3,4-di-Me) Ph(3,4-di-F) Ph(3,4,5-tri-OMe) Ph(2-I) Ph(3-I) Ph(4-I) Ph(2-Et) Ph(3-Et) Ph(4-Et) CH₂CH₂OCH₂CH₃ CH(CH₃)CH₂OCH₃ Ph(2-OCF₃) Ph(3-OCF₃) Ph(4-OCF₃) Ph(2-Me-3-F) Ph(2-Me-4-F) Ph(2-Me-5-F) Ph(2-F-3-Me) Ph(2-F-4-Me) Ph(2-F-5-Me) Ph(3-F-4-Me) Ph(3-F-5-Me) Ph(3-Me-4-F) CH₂CH₂CH₂OCH₃ CH₂CH₂CH₂OCH₂CH₃ CH₂(thp-2-yl) CH₂(thp-4-yl) CH₂CH₂CH═CH₂ CH₂C≡CH CH₂CH₂SCH₃ CH₂CH₂SOCH₃ CH₂CH₂SO₂CH₃ CH₂CH₂CH₂SCH₃ CH₂CH₂CH₂SOCH₃ CH₂CH₂CH₂SO₂CH₃

The present disclosure also includes Tables 1BB through 57BB, each of which is constructed the same as Table 27 above except that the row heading in Table 27 (i.e. “R² is Ph”) is replaced with the respective row headings shown below. For example, in Table 1BB the row heading is “R² is Me”, and R¹ is as defined in Table 27 above. Thus, the first entry in Table 1BB specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R¹ is Me; R² is Me; R³ is OH; A is A-1; B¹ is C-1; B² is C-3; B³ is C-1; and each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is H. Tables 2BB through 57BB are constructed similarly.

Table Row Heading  1BB R² is Me  2BB R² is Et  3BB R² is n-Pr  4BB R² is c-Pr  5BB R² is SMe  6BB R² is SO₂Me  7BB R² is CF₃  8BB R² is Ph(2-Cl)  9BB R² is Ph(3-Cl) 10BB R² is Ph(4-Cl) 11BB R² is Ph(2-Me) 12BB R² is Ph(3-Me) 13BB R² is Ph(4-Me) 14BB R² is Ph(2-OMe) 15BB R² is Ph(3-OMe) 16BB R² is Ph(4-OMe) 17BB R² is Ph(2-F) 18BB R² is Ph(3-F) 19BB R² is Ph(4-F) 20BB R² is OMe 21BB R² is OEt 22BB R² is CH₂Ph 23BB R² is 2-pyridinyl 24BB R² is 3-pyridinyl 25BB R² is 4-pyridinyl 26BB H 27BB Ph(3,5-di-F) 28BB Ph(3,4-di-F) 29BB Ph(3,4,5-tri-F) 30BB Ph(2,3-di-F) 31BB Ph(3-CF₃) 32BB Ph(4-CF₃) 33BB Ph(3,5-di-CF₃) 34BB n-Bu 35BB CH₂OCH₃ 36BB CH₂CH₂OCH₃ 37BB CH₂CH₂CF₃ 38BB CH₂CF₃ 39BB n-pent 40BB c-pent 41BB c-Hex 42BB n-Hex 43BB thp-4-yl 44BB Ph(2-CN) 45BB Ph(3-CN) 46BB Ph(4-CN) 47BB Ph(2-C≡CH) 48BB Ph(3-C≡CH) 49BB Ph(4-C≡CH) 50BB Ph(3-Me, 2-F) 51BB Ph(3-Me-4-F) 52BB Ph(3-Me, 5-F) 53BB Ph(3-Me, 6-F) 54BB Ph(3-F, 2-Me) 55BB Ph(3-F-4-Me) 56BB Ph(3-F-5-Me) 57BB Ph(3-F, 6-Me)

TABLE 28 Table 28 is constructed the same as Table 27 except the structure is replaced with

TABLE 29 Table 29 is constructed the same as Table 27 except the structure is replaced with

TABLE 30 Table 30 is constructed the same as Table 27 except the structure is replaced with

TABLE 31 Table 31 is constructed the same as Table 27 except the structure is replaced with

TABLE 32 Table 32 is constructed the same as Table 27 except the structure is replaced with

TABLE 33 Table 32 is constructed the same as Table 27 except the structure is replaced with

TABLE 34

  R² is Ph R¹ Me Et n-Pr i-Pr c-Pr n-Bu i-Bu s-Bu c-Bu t-Bu n-pent c-Pent n-Hex c-Hex Ph CH₂-c-Pr CH₂-c-Bu CH₂SPh CH₂SCH₃ CH₂CF₃ CH₂Ph CH₂CHC(CH₃)₂ CH₂CH₂C≡CH CH₂CH═CCl₂ CH₂CH═CF₂ CH₂CF═CF₂ CH₂CCl═CCl₂ CH₂C≡CCH₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ CH₂SO₂CH₃ CH₂SCH₂CH₃ Ph(2,3-di-OMe) CH₂SO₂-n-Pr CH₂CH₂SO₂Et Ph(2,4-di-OMe) Ph(2,5-di-OMe) Ph(2,6-di-OMe) Ph(3,5-di-OMe) CH₂Ph(2-OMe) CH₂Ph(3-OMe) CH₂Ph(4-OMe) CH₂SO₂Ph CH₂SCH₂Ph CH₂CH₂SEt Ph(2,4-di-Cl) Ph(2,5-di-Cl) Ph(2,6-di-C1) Ph(3,5-di-C1) Ph(2,3-di-Me) Ph(2,4-di-Me) Ph(2,5-di-Me) Ph(2,6-di-Me) Ph(3,5-di-Me) CH₂-c-Hex Ph(2,3-di-F) Ph(2,4-di-F) Ph(2,5-di-F) Ph(2,6-di-F) CH₂CH₂CF₃ CH₂C≡CH Ph(2,3-di-Cl) Ph(3-NO₂) Ph(2-Cl) Ph(3-Cl) Ph(4-Cl) Ph(2-Me) Ph(3-Me) CH₂OCH₃ CH₂CH═CH₂ Ph(2-OMe) Ph(3-OMe) Ph(4-OMe) Ph(2-CN) Ph(3-CN) Ph(4-CN) Ph(2-F) Ph(3-F) Ph(4-F) CH₂S-n-Pr CH₂-c-Pent CH₂CF₂CF₃ CH═CH₂ Ph(2-NO₂) Ph(4-NO₂) Ph(2-CF₃) Ph(3-CF₃) Ph(4-CF₃) Ph(2-Br) Ph(3-Br) Ph(4-Br) CH₂Ph(2-Me) CH₂Ph(3-Me) CH₂Ph(4-Me) CH₂Ph(2-Cl) CH₂Ph(3-Cl) CH₂Ph(4-Cl) CH₂CH₂SO₂Me CH₂OCH₂OCH₃ CH₂OCH₂CH₂OCH₃ CH₂C(CH₃)C(CH₃)₂ Ph(4-Me) CH₂CH₂SMe Ph(3,5-di-F) The present disclosure also includes Tables 1K through 4K, each of which is constructed the same as Table 11 above except that the row heading in Table 11 (i.e. “R² is Ph”) is replaced with the respective row headings shown below. For example, in Table 1K the row heading is “R² is Ph”, and R¹ is as defined in Table 11 above. Thus, the first entry in Table 1K specifically discloses a compound of Formula 1P wherein X is N, Y is C(O), R¹ is Me; R² is c-Pr; R³ is OH; A is A-1; B¹ is C-1; B² is C-3; B³ is C-1; and each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is H. Tables 2K through 4K are constructed similarly.

Table Row Heading 1K R² is c-Pr 2K R² is SMe 3K R² is SO₂Me 4K R² is CF₃

TABLE 35

  R² is Ph R¹ Me Et n-Pr i-Pr c-Pr n-Bu i-Bu s-Bu c-Bu t-Bu n-pent c-Pent n-Hex c-Hex Ph CH₂-c-Pr CH₂-c-Bu CH₂SPh CH₂SCH₃ CH₂CF₃ CH₂Ph CH₂CHC(CH₃)₂ CH₂CH₂C≡CH CH₂CH═CCl₂ CH₂CH═CF₂ CH₂CF═CF₂ CH₂CCl═CCl₂ CH₂C≡CCH₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ CH₂SO₂CH₃ CH₂SCH₂CH₃ Ph(2,3-di-OMe) CH₂SO₂-n-Pr CH₂CH₂SO₂Et Ph(2,4-di-OMe) Ph(2,5-di-OMe) Ph(2,6-di-OMe) Ph(3,5-di-OMe) CH₂Ph(2-OMe) CH₂Ph(3-OMe) CH₂Ph(4-OMe) CH₂SO₂Ph CH₂SCH₂Ph CH₂CH₂SEt Ph(2,4-di-Cl) Ph(2,5-di-Cl) Ph(2,6-di-C1) Ph(3,5-di-C1) Ph(2,3-di-Me) Ph(2,4-di-Me) Ph(2,5-di-Me) Ph(2,6-di-Me) Ph(3,5-di-Me) CH₂-c-Hex Ph(2,3-di-F) Ph(2,4-di-F) Ph(2,5-di-F) Ph(2,6-di-F) CH₂CH₂CF₃ CH₂C≡CH Ph(2,3-di-Cl) Ph(3-NO₂) Ph(2-Cl) Ph(3-Cl) Ph(4-Cl) Ph(2-Me) Ph(3-Me) CH₂OCH₃ CH₂CH═CH₂ Ph(2-OMe) Ph(3-OMe) Ph(4-OMe) Ph(2-CN) Ph(3-CN) Ph(4-CN) Ph(2-F) Ph(3-F) Ph(4-F) CH₂S-n-Pr CH₂-c-Pent CH₂CF₂CF₃ CH═CH₂ Ph(2-NO₂) Ph(4-NO₂) Ph(2-CF₃) Ph(3-CF₃) Ph(4-CF₃) Ph(2-Br) Ph(3-Br) Ph(4-Br) CH₂Ph(2-Me) CH₂Ph(3-Me) CH₂Ph(4-Me) CH₂Ph(2-Cl) CH₂Ph(3-Cl) CH₂Ph(4-Cl) CH₂CH₂SO₂Me CH₂OCH₂OCH₃ CH₂OCH₂CH₂OCH₃ CH₂C(CH₃)C(CH₃)₂ Ph(4-Me) CH₂CH₂SMe Ph(3,5-di-F) The present disclosure also includes Tables 1L through 11L, each of which is constructed the same as Table 12 above except that the row heading in Table 12 (i.e. “R² is Ph”) is replaced with the respective row headings shown below. For example, in Table 1L the row heading is “R² is Ph”, and R¹ is as defined in Table 12 above. Thus, the first entry in Table 1L specifically discloses a compound of Formula 1P wherein X is CH; Y is S(O)₂; R¹ is Me and R² is c-Pr; R³ is OH; A is A-1; B¹ is C-1; B² is C-3; B³ is C-1; and each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is H. Tables 2L through 11L are constructed similarly.

Table Row Heading  1L R² is c-Pr  2L R² is n-Pr  3L R² is SMe  4L R² is SO₂Me  5L R² is CF₃  6L R² Ph(2-Cl)  7L R² Ph(3-Cl)  8L R² is Ph(4-Cl)  9L R² is Ph(2-Me) 10L R² is Ph(3-Me) 11L R² is Ph(4-Me)

A compound of this invention will generally be used as a herbicidal active ingredient in a composition, i.e. formulation, with at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents, which serves as a carrier. The formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature.

Useful formulations include both liquid and solid compositions. Liquid compositions include solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions) and the like, which optionally can be thickened into gels. The general types of aqueous liquid compositions are soluble concentrate, suspension concentrate, capsule suspension, concentrated emulsion, microemulsion and suspo-emulsion. The general types of nonaqueous liquid compositions are emulsifiable concentrate, microemulsifiable concentrate, dispersible concentrate and oil dispersion.

The general types of solid compositions are dusts, powders, granules, pellets, prills, pastilles, tablets, filled films (including seed coatings) and the like, which can be water-dispersible (“wettable”) or water-soluble. Films and coatings formed from film-forming solutions or flowable suspensions are particularly useful for seed treatment. Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or “overcoated”). Encapsulation can control or delay release of the active ingredient. An emulsifiable granule combines the advantages of both an emulsifiable concentrate formulation and a dry granular formulation. High-strength compositions are primarily used as intermediates for further formulation.

Sprayable formulations are typically extended in a suitable medium before spraying. Such liquid and solid formulations are formulated to be readily diluted in the spray medium, usually water. Spray volumes can range from about from about one to several thousand liters per hectare, but more typically are in the range from about ten to several hundred liters per hectare. Sprayable formulations can be tank mixed with water or another suitable medium for foliar treatment by aerial or ground application, or for application to the growing medium of the plant. Liquid and dry formulations can be metered directly into drip irrigation systems or metered into the furrow during planting.

The formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.

Weight Percent Active Ingredient Diluent Surfactant Water-Dispersible and Water- 0.001-90      0-99.999  0-15 soluble Granules, Tablets and Powders Oil Dispersions, Suspensions,  1-50 40-99  0-50 Emulsions, Solutions (including Emulsifiable Concentrates) Dusts  1-25 70-99 0-5 Granules and Pellets 0.001-99      5-99.999  0-15 High Strength Compositions 90-99  0-10 0-2

Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose), silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate. Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, N.J. .

Liquid diluents include, for example, water, N,N-dimethylalkanamides (e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide, N-alkylpyrrolidones (e.g., N-methylpyrrolidinone), ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffins (e.g., white mineral oils, normal paraffins, isoparaffins), alkylbenzenes, alkylnaphthalenes, glycerine, glycerol triacetate, sorbitol, aromatic hydrocarbons, dearomatized aliphatics, alkylbenzenes, alkylnaphthalenes, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, acetates such as isoamyl acetate, hexyl acetate, heptyl acetate, octyl acetate, nonyl acetate, tridecyl acetate and isobornyl acetate, other esters such as alkylated lactate esters, dibasic esters and γ-butyrolactone, and alcohols, which can be linear, branched, saturated or unsaturated, such as methanol, ethanol, n-propanol, isopropyl alcohol, n-butanol, isobutyl alcohol, n-hexanol, 2-ethylhexanol, n-octanol, decanol, isodecyl alcohol, isooctadecanol, cetyl alcohol, lauryl alcohol, tridecyl alcohol, oleyl alcohol, cyclohexanol, tetrahydrofurfuryl alcohol, diacetone alcohol and benzyl alcohol. Liquid diluents also include glycerol esters of saturated and unsaturated fatty acids (typically C₆-C₂₂), such as plant seed and fruit oils (e.g., oils of olive, castor, linseed, sesame, corn (maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palm kernel), animal-sourced fats (e.g., beef tallow, pork tallow, lard, cod liver oil, fish oil), and mixtures thereof. Liquid diluents also include alkylated fatty acids (e.g., methylated, ethylated, butylated) wherein the fatty acids may be obtained by hydrolysis of glycerol esters from plant and animal sources, and can be purified by distillation. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.

The solid and liquid compositions of the present invention often include one or more surfactants. When added to a liquid, surfactants (also known as “surface-active agents”) generally modify, most often reduce, the surface tension of the liquid. Depending on the nature of the hydrophilic and lipophilic groups in a surfactant molecule, surfactants can be useful as wetting agents, dispersants, emulsifiers or defoaming agents.

Surfactants can be classified as nonionic, anionic or cationic. Nonionic surfactants useful for the present compositions include, but are not limited to: alcohol alkoxylates such as alcohol alkoxylates based on natural and synthetic alcohols (which may be branched or linear) and prepared from the alcohols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof; amine ethoxylates, alkanolamides and ethoxylated alkanolamides; alkoxylated triglycerides such as ethoxylated soybean, castor and rapeseed oils; alkylphenol alkoxylates such as octylphenol ethoxylates, nonylphenol ethoxylates, dinonyl phenol ethoxylates and dodecyl phenol ethoxylates (prepared from the phenols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); block polymers prepared from ethylene oxide or propylene oxide and reverse block polymers where the terminal blocks are prepared from propylene oxide; ethoxylated fatty acids; ethoxylated fatty esters and oils; ethoxylated methyl esters; ethoxylated tristyrylphenol (including those prepared from ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); fatty acid esters, glycerol esters, lanolin-based derivatives, polyethoxylate esters such as polyethoxylated sorbitan fatty acid esters, polyethoxylated sorbitol fatty acid esters and polyethoxylated glycerol fatty acid esters; other sorbitan derivatives such as sorbitan esters; polymeric surfactants such as random copolymers, block copolymers, alkyd peg (polyethylene glycol) resins, graft or comb polymers and star polymers; polyethylene glycols (pegs); polyethylene glycol fatty acid esters; silicone-based surfactants; and sugar-derivatives such as sucrose esters, alkyl polyglycosides and alkyl polysaccharides.

Useful anionic surfactants include, but are not limited to: alkylaryl sulfonic acids and their salts; carboxylated alcohol or alkylphenol ethoxylates; diphenyl sulfonate derivatives; lignin and lignin derivatives such as lignosulfonates; maleic or succinic acids or their anhydrides; olefin sulfonates; phosphate esters such as phosphate esters of alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates and phosphate esters of styryl phenol ethoxylates; protein-based surfactants; sarcosine derivatives; styryl phenol ether sulfate; sulfates and sulfonates of oils and fatty acids; sulfates and sulfonates of ethoxylated alkylphenols; sulfates of alcohols; sulfates of ethoxylated alcohols; sulfonates of amines and amides such as N,N-alkyltaurates; sulfonates of benzene, cumene, toluene, xylene, and dodecyl and tridecylbenzenes; sulfonates of condensed naphthalenes; sulfonates of naphthalene and alkyl naphthalene; sulfonates of fractionated petroleum; sulfosuccinamates; and sulfosuccinates and their derivatives such as dialkyl sulfosuccinate salts.

Useful cationic surfactants include, but are not limited to: amides and ethoxylated amides; amines such as N-alkyl propanediamines, tripropylenetriamines and dipropylenetetramines, and ethoxylated amines, ethoxylated diamines and propoxylated amines (prepared from the amines and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); amine salts such as amine acetates and diamine salts; quaternary ammonium salts such as quaternary salts, ethoxylated quaternary salts and diquaternary salts; and amine oxides such as alkyldimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides.

Also useful for the present compositions are mixtures of nonionic and anionic surfactants or mixtures of nonionic and cationic surfactants. Nonionic, anionic and cationic surfactants and their recommended uses are disclosed in a variety of published references including McCutcheon's Emulsifiers and Detergents, annual American and International Editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; and A. S. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition, John Wiley and Sons, New York, 1987.

Compositions of this invention may also contain formulation auxiliaries and additives, known to those skilled in the art as formulation aids (some of which may be considered to also function as solid diluents, liquid diluents or surfactants). Such formulation auxiliaries and additives may control: pH (buffers), foaming during processing (antifoams such polyorganosiloxanes), sedimentation of active ingredients (suspending agents), viscosity (thixotropic thickeners), in-container microbial growth (antimicrobials), product freezing (antifreezes), color (dyes/pigment dispersions), wash-off (film formers or stickers), evaporation (evaporation retardants), and other formulation attributes. Film formers include, for example, polyvinyl acetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers and waxes. Examples of formulation auxiliaries and additives include those listed in McCutcheon's Volume 2. Functional Materials, annual International and North American editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; and PCT Publication WO 03/024222.

The compound of Formula 1 and any other active ingredients are typically incorporated into the present compositions by dissolving the active ingredient in a solvent or by grinding in a liquid or dry diluent. Solutions, including emulsifiable concentrates, can be prepared by simply mixing the ingredients. If the solvent of a liquid composition intended for use as an emulsifiable concentrate is water-immiscible, an emulsifier is typically added to emulsify the active-containing solvent upon dilution with water. Active ingredient slurries, with particle diameters of up to 2,000 μm can be wet milled using media mills to obtain particles with average diameters below 3 μm. Aqueous slurries can be made into finished suspension concentrates (see, for example, U.S. Pat. No. 3,060,084) or further processed by spray drying to form water-dispersible granules. Dry formulations usually require dry milling processes, which produce average particle diameters in the 2 to 10 μm range. Dusts and powders can be prepared by blending and usually grinding (such as with a hammer mill or fluid-energy mill). Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, “Agglomeration”, Chemical Engineering, Dec. 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546. Pellets can be prepared as described in U.S. Pat. No. 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in U.S. Pat. No. 4,144,050, U.S. Pat. No. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. Pat. No. 5,180,587, U.S. Pat. No. 5,232,701 and U.S. Pat. No. 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. 3,299,566.

For further information regarding the art of formulation, see T. S. Woods, “The Formulator's Toolbox—Product Forms for Modern Agriculture” in Pesticide Chemistry and Bioscience, The Food-Environment Challenge, T. Brooks and T. R. Roberts, Eds., Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120-133. See also U.S. Pat. No. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41; U.S. Pat. No. 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81-96; Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989; and Developments in formulation technology, PJB Publications, Richmond, U K, 2000.

In the following Examples, all percentages are by weight and all formulations are prepared in conventional ways. Compound numbers refer to compounds in Index Tables A-B. Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following Examples are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever. Percentages are by weight except where otherwise indicated.

Example A High Strength Concentrate

Compound 4 98.5% silica aerogel  0.5% synthetic amorphous fine silica  1.0%

Example B Wettable Powder

Compound 2 65.0% dodecylphenol polyethylene glycol ether  2.0% sodium ligninsulfonate  4.0% sodium silicoaluminate  6.0% montmorillonite (calcined) 23.0%

Example C Granule

Compound 12 10.0% attapulgite granules (low volatile matter, 0.71/0.30 mm; 90.0% U.S.S. No. 25-50 sieves)

Example D Extruded Pellet

Compound 8 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate  5.0% sodium alkylnaphthalenesulfonate  1.0% calcium/magnesium bentonite 59.0%

Example E Emulsifiable Concentrate

Compound 2 10.0% polyoxyethylene sorbitol hexoleate 20.0% C₆-C₁₀ fatty acid methyl ester 70.0%

Example F Microemulsion

Compound 12  5.0% polyvinylpyrrolidone-vinyl acetate copolymer 30.0% alkylpolyglycoside 30.0% glyceryl monooleate 15.0% Water 20.0%

These compounds generally show highest activity for early postemergence weed control (i.e. applied when the emerged weed seedlings are still young) and preemergence weed control (i.e. applied before weed seedlings emerge from the soil). Many of them have utility for broad-spectrum pre- and/or postemergence weed control in areas where complete control of all vegetation is desired such as around fuel storage tanks, industrial storage areas, parking lots, drive-in theaters, air fields, river banks, irrigation and other waterways, around billboards and highway and railroad structures. Many of the compounds of this invention, by virtue of selective metabolism in crops versus weeds, or by selective activity at the locus of physiological inhibition in crops and weeds, or by selective placement on or within the environment of a mixture of crops and weeds, are useful for the selective control of grass and broadleaf weeds within a crop/weed mixture. One skilled in the art will recognize that the preferred combination of these selectivity factors within a compound or group of compounds can readily be determined by performing routine biological and/or biochemical assays. Compounds of this invention may show tolerance to important agronomic crops including, but not limited to, alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize), sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato, perennial plantation crops including coffee, cocoa, oil palm, rubber, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, pineapple, hops, tea and forests such as eucalyptus and conifers (e.g., loblolly pine), and turf species (e.g., Kentucky bluegrass, St. Augustine grass, Kentucky fescue and Bermuda grass). Compounds of the invention are particularly useful for selective control of weeds in wheat, barley, and particularly maize, soybean, cotton and perennial plantation crops such as sugarcane and citrus. Compounds of this invention can be used in crops genetically transformed or bred to incorporate resistance to herbicides, express proteins toxic to invertebrate pests (such as Bacillus thuringiensis toxin), and/or express other useful traits. Those skilled in the art will appreciate that not all compounds are equally effective against all weeds. Alternatively, the subject compounds are useful to modify plant growth.

As the compounds of the invention have both postemergent and preemergent herbicidal activity, to control undesired vegetation by killing or injuring the vegetation or reducing its growth, the compounds can be usefully applied by a variety of methods involving contacting a herbicidally effective amount of a compound of the invention, or a composition comprising said compound and at least one of a surfactant, a solid diluent or a liquid diluent, to the foliage or other part of the undesired vegetation or to the environment of the undesired vegetation such as the soil or water in which the undesired vegetation is growing or which surrounds the seed or other propagule of the undesired vegetation.

A herbicidally effective amount of the compounds of this invention is determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally effective amount of a compound of this invention is about 0.001 to 20 kg/ha with a typical range of about 0.004 to 1 kg/ha. One skilled in the art can easily determine the herbicidally effective amount necessary for the desired level of weed control.

Compounds of this invention can also be mixed with one or more other biologically active compounds or agents including herbicides, herbicide safeners, fungicides, insecticides, nematocides, bactericides, acaricides, growth regulators such as insect molting inhibitors and rooting stimulants, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants, plant nutrients, other biologically active compounds or entomopathogenic bacteria, virus or fungi to form a multi-component pesticide giving an even broader spectrum of agricultural protection. Mixtures of the compounds of the invention with other herbicides can broaden the spectrum of activity against additional weed species, and suppress the proliferation of any resistant biotypes. Thus the present invention also pertains to a composition comprising a compound of Formula 1 (in a herbicidally effective amount) and at least one additional biologically active compound or agent (in a biologically effective amount) and can further comprise at least one of a surfactant, a solid diluent or a liquid diluent. The other biologically active compounds or agents can be formulated in compositions comprising at least one of a surfactant, solid or liquid diluent. For mixtures of the present invention, one or more other biologically active compounds or agents can be formulated together with a compound of Formula 1, to form a premix, or one or more other biologically active compounds or agents can be formulated separately from the compound of Formula 1, and the formulations combined together before application (e.g., in a spray tank) or, alternatively, applied in succession.

A mixture of one or more of the following herbicides with a compound of this invention may be particularly useful for weed control: acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal), alachlor, alloxydim, ametryn, amicarbazone, amidosulfuron, aminocyclopyrachlor and its esters (e.g., methyl, ethyl) and salts (e.g., sodium, potassium), aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyrone, bifenox, bilanafos, bispyribac and its sodium salt, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil octanoate, butachlor, butafenacil, butamifos, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone-ethyl, catechin, chlomethoxyfen, chloramben, chlorbromuron, chlorflurenol-methyl, chloridazon, chlorimuron-ethyl, chlorotoluron, chlorpropham, chlorsulfuron, chlorthal-dimethyl, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, clefoxydim, clethodim, clodinafop-propargyl, clomazone, clomeprop, clopyralid, clopyralid-olamine, cloransulam-methyl, cumyluron, cyanazine, cycloate, cyclosulfamuron, cycloxydim, cyhalofop-butyl, 2,4-D and its butotyl, butyl, isoctyl and isopropyl esters and its dimethylammonium, diolamine and trolamine salts, daimuron, dalapon, dalapon-sodium, dazomet, 2,4-DB and its dimethylammonium, potassium and sodium salts, desmedipham, desmetryn, dicamba and its diglycolammonium, dimethylammonium, potassium and sodium salts, dichlobenil, dichlorprop, diclofop-methyl, diclosulam, difenzoquat metilsulfate, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin, dimethylarsinic acid and its sodium salt, dinitramine, dinoterb, diphenamid, diquat dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fentrazamide, fenuron, fenuron-TCA, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron, fluoroglycofen-ethyl, flupoxam, flupyrsulfuron-methyl and its sodium salt, flurenol, flurenol-butyl, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet-methyl, fomesafen, foramsulfuron, fosamine-ammonium, glufosinate, glufosinate-ammonium, glyphosate and its salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium) and trimesium (alternatively named sulfosate), halo sulfuron-methyl, haloxyfop-etotyl, haloxyfop-methyl, hexazinone, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan, iodosulfuron-methyl, ioxynil, ioxynil octanoate, ioxynil-sodium, isoproturon, isouron, isoxaben, isoxaflutole, isoxachlortole, lactofen, lenacil, linuron, maleic hydrazide, MCPA and its salts (e.g., MCPA-dimethylammonium, MCPA-potassium and MCPA-sodium, esters (e.g., MCPA-2-ethylhexyl, MCPA-butotyl) and thioesters (e.g., MCPA-thioethyl), MCPB and its salts (e.g., MCPB-sodium) and esters (e.g., MCPB-ethyl), mecoprop, mecoprop-P, mefenacet, mefluidide, mesosulfuron-methyl, mesotrione, metam-sodium, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methylarsonic acid and its calcium, monoammonium, monosodium and disodium salts, methyldymron, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron-methyl, molinate, monolinuron, naproanilide, napropamide, naptalam, neburon, nicosulfuron, norflurazon, orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat dichloride, pebulate, pelargonic acid, pendimethalin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid, pethoxyamid, phenmedipham, picloram, picloram-potassium, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazogyl, pyrazolynate, pyrazoxyfen, pyrazosulfuron-ethyl, pyribenzoxim, pyributicarb, pyridate, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron-methyl, sulfosulfuron, 2,3,6-TBA, TCA, TCA-sodium, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbumeton, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thifensulfuron-methyl, thiobencarb, tiocarbazil, topramezone, tralkoxydim, tri-allate, triasulfuron, triaziflam, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-triethylammonium, tridiphane, trietazine, trifloxysulfuron, trifluralin, triflusulfuron-methyl, tritosulfuron and vernolate. Other herbicides also include bioherbicides such as Alternaria destruens Simmons, Colletotrichum gloeosporiodes (Penz.) Penz. & Sacc., Drechsiera monoceras (MTB-951), Myrothecium verrucaria (Albertini & Schweinitz) Ditmar: Fries, Phytophthora palmivora (Butl.) Butl. and Puccinia thlaspeos Schub.

Compounds of this invention can also be used in combination with plant growth regulators such as aviglycine, N-(phenylmethyl)-1H-purin-6-amine, epocholeone, gibberellic acid, gibberellin A₄ and A₇, harpin protein, mepiquat chloride, prohexadione calcium, prohydrojasmon, sodium nitrophenolate and trinexapac-methyl, and plant growth modifying organisms such as Bacillus cereus strain BP01.

General references for agricultural protectants (i.e. herbicides, herbicide safeners, insecticides, fungicides, nematocides, acaricides and biological agents) include The Pesticide Manual, 13th Edition, C. D. S. Tomlin, Ed., British Crop Protection Council, Farnham, Surrey, U. K., 2003 and The BioPesticide Manual, 2nd Edition, L. G. Copping, Ed., British Crop Protection Council, Farnham, Surrey, U. K., 2001.

For embodiments where one or more of these various mixing partners are used, the weight ratio of these various mixing partners (in total) to the compound of Formula 1 is typically between about 1:3000 and about 3000:1. Of note are weight ratios between about 1:300 and about 300:1 (for example ratios between about 1:30 and about 30:1). One skilled in the art can easily determine through simple experimentation the biologically effective amounts of active ingredients necessary for the desired spectrum of biological activity. It will be evident that including these additional components may expand the spectrum of weeds controlled beyond the spectrum controlled by the compound of Formula 1 alone.

In certain instances, combinations of a compound of this invention with other biologically active (particularly herbicidal) compounds or agents (i.e. active ingredients) can result in a greater-than-additive (i.e. synergistic) effect on weeds and/or a less-than-additive effect (i.e. safening) on crops or other desirable plants. Reducing the quantity of active ingredients released in the environment while ensuring effective pest control is always desirable. Ability to use greater amounts of active ingredients to provide more effective weed control without excessive crop injury is also desirable. When synergism of herbicidal active ingredients occurs on weeds at application rates giving agronomically satisfactory levels of weed control, such combinations can be advantageous for reducing crop production cost and decreasing environmental load. When safening of herbicidal active ingredients occurs on crops, such combinations can be advantageous for increasing crop protection by reducing weed competition.

Of note is a combination of a compound of the invention with at least one other herbicidal active ingredient. Of particular note is such a combination where the other herbicidal active ingredient has different site of action from the compound of the invention. In certain instances, a combination with at least one other herbicidal active ingredient having a similar spectrum of control but a different site of action will be particularly advantageous for resistance management. Thus, a composition of the present invention can further comprise (in a herbicidally effective amount) at least one additional herbicidal active ingredient having a similar spectrum of control but a different site of action.

Compounds of this invention can also be used in combination with herbicide safeners such as allidochlor, benoxacor, BCS (1-bromo-4-[(chloromethyl)sulfonyl]benzene), cloquintocet-mexyl, cyometrinil, cyprosulfonamide, dichlormid, 4-(dichloroacetyl)-1-oxa-4-azospiro[4.5]decane (MON 4660), 2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG 191), dicyclonon, dietholate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone ((4-methoxy-3-methylphenyl)(3-methylphenyl)methanone), naphthalic anhydride (1,8-naphthalic anhydride) and oxabetrinil to increase safety to certain crops. Antidotally effective amounts of the herbicide safeners can be applied at the same time as the compounds of this invention, or applied as seed treatments. Therefore an aspect of the present invention relates to a herbicidal mixture comprising a compound of this invention and an antidotally effective amount of a herbicide safener. Seed treatment is particularly useful for selective weed control, because it physically restricts antidoting to the crop plants. Therefore a particularly useful embodiment of the present invention is a method for selectively controlling the growth of undesired vegetation in a crop comprising contacting the locus of the crop with a herbicidally effective amount of a compound of this invention wherein seed from which the crop is grown is treated with an antidotally effective amount of safener. Antidotally effective amounts of safeners can be easily determined by one skilled in the art through simple experimentation.

Of note is a composition comprising a compound of the invention (in a herbicidally effective amount), at least one additional active ingredient selected from the group consisting of other herbicides and herbicide safeners (in an effective amount), and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.

Preferred for better control of undesired vegetation (e.g., lower use rate such as from synergism, broader spectrum of weeds controlled, or enhanced crop safety) or for preventing the development of resistant weeds are mixtures of a compound of this invention with a herbicide selected from the group consisting of 2,4-D, ametryne, aminocyclopyrachlor, aminopyralid, atrazine, bromacil, bromoxynil, bromoxynil octanoate, carfentrazone-ethyl, chlorimuron-ethyl, chlorsulfuron, clopyralid, clopyralid-olamine, dicamba and its diglycolammonium, dimethylammonium, potassium and sodium salts, diflufenican, dimethenamid, dimethenamid-P, diuron, florasulam, flufenacet, flumetsulam, flumioxazin, flupyrsulfuron-methyl, flupyrsulfuron-methyl-sodium, fluroxypyr, glyphosate (particularly glyphosate-isopropylammonium, glyphosate-sodium, glyphosate-potassium, glyphosate-trimesium), hexazinone, imazamethabenz-methyl, imazaquin, imazethapyr, iodosulfuron-methyl, lactofen, lenacil, linuron, MCPA and its dimethylammonium, potassium and sodium salts, MCPA-isoctyl, MCPA-thioethyl, mesosulfuron-methyl, S-metolachlor, metribuzin, metsulfuron-methyl, nicosulfuron, oxyfluorfen, pendimethalin, pinoxaden, pronamide, prosulfuron, pyroxasulfone, pyroxsulam, quinclorac, rimsulfuron, saflufenacil, sulfentrazone, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, triclopyr, triclopyr-butotyl, and triclopyr-triethylammonium. Specifically preferred mixtures (compound numbers refer to compounds in Index Table A) are selected from the group: compound 2 and 2,4-D; compound 4 and 2,4-D; compound 8 and 2,4-D; compound 12 and 2,4-D; compound 2 and ametryne; compound 4 and ametryne; compound 8 and ametryne; compound 12 and ametryne; compound 2 and aminocyclopyrachlor; compound 4 and aminocyclopyrachlor; compound 8 and aminocyclopyrachlor; compound 12 and aminocyclopyrachlor; compound 2 and aminopyralid; compound 4 and aminopyralid; compound 8 and aminopyralid; compound 12 and aminopyralid; compound 2 and atrazine; compound 4 and atrazine; compound 8 and atrazine; compound 12 and atrazine; compound 2 and bromacil; compound 4 and bromacil; compound 8 and bromacil; compound 12 and bromacil; compound 2 and bromoxynil; compound 4 and bromoxynil; compound 8 and bromoxynil; compound 12 and bromoxynil; compound 2 and bromoxynil octanoate; compound 4 and bromoxynil octanoate; compound 8 and bromoxynil octanoate; compound 12 and bromoxynil octanoate; compound 2 and carfentrazone-ethyl; compound 4 and carfentrazone-ethyl; compound 8 and carfentrazone-ethyl; compound 12 and carfentrazone-ethyl; compound 2 and chlorimuron-ethyl; compound 4 and chlorimuron-ethyl; compound 8 and chlorimuron-ethyl; compound 12 and chlorimuron-ethyl; compound 2 and chlorsulfuron; compound 4 and chlorsulfuron; compound 8 and chlorsulfuron; compound 12 and chlorsulfuron; compound 2 and clopyralid; compound 4 and clopyralid; compound 8 and clopyralid; compound 12 and clopyralid; compound 2 and clopyralid-olamine; compound 4 and clopyralid-olamine; compound 8 and clopyralid-olamine; compound 12 and clopyralid-olamine; compound 2 and dicamba; compound 4 and dicamba; compound 8 and dicamba; compound 12 and dicamba; compound 2 and diflufenican; compound 4 and diflufenican; compound 8 and diflufenican; compound 12 and diflufenican; compound 2 and dimethenamid; compound 4 and dimethenamid; compound 8 and dimethenamid; compound 12 and dimethenamid; compound 2 and dimethenamid-P; compound 4 and dimethenamid-P; compound 8 and dimethenamid-P; compound 12 and dimethenamid-P; compound 2 and diuron; compound 4 and diuron; compound 8 and diuron; compound 12 and diuron; compound 2 and florasulam; compound 4 and florasulam; compound 8 and florasulam; compound 12 and florasulam; compound 2 and flufenacet; compound 4 and flufenacet; compound 8 and flufenacet; compound 12 and flufenacet; compound 2 and flumetsulam; compound 4 and flumetsulam; compound 8 and flumetsulam; compound 12 and flumetsulam; compound 2 and flumioxazin; compound 4 and flumioxazin; compound 8 and flumioxazin; compound 12 and flumioxazin; compound 2 and flupyrsulfuron-methyl; compound 4 and flupyrsulfuron-methyl; compound 8 and flupyrsulfuron-methyl; compound 12 and flupyrsulfuron-methyl; compound 2 and flupyrsulfuron-methyl-sodium; compound 4 and flupyrsulfuron-methyl-sodium; compound 8 and flupyrsulfuron-methyl-sodium; compound 12 and flupyrsulfuron-methyl-sodium; compound 2 and fluroxypyr; compound 4 and fluroxypyr; compound 8 and fluroxypyr; compound 12 and fluroxypyr; compound 2 and glyphosate; compound 4 and glyphosate; compound 8 and glyphosate; compound 12 and glyphosate; compound 2 and hexazinone; compound 4 and hexazinone; compound 8 and hexazinone; compound 12 and hexazinone; compound 2 and imazamethabenz-methyl; compound 4 and imazamethabenz-methyl; compound 8 and imazamethabenz-methyl; compound 12 and imazamethabenz-methyl; compound 2 and imazaquin; compound 4 and imazaquin; compound 8 and imazaquin; compound 12 and imazaquin; compound 2 and imazethapyr; compound 4 and imazethapyr; compound 8 and imazethapyr; compound 12 and imazethapyr; compound 2 and iodosulfuron-methyl; compound 4 and iodosulfuron-methyl; compound 8 and iodosulfuron-methyl; compound 12 and iodosulfuron-methyl; compound 2 and lactofen; compound 4 and lactofen; compound 8 and lactofen; compound 12 and lactofen; compound 2 and lenacil; compound 4 and lenacil; compound 8 and lenacil; compound 12 and lenacil; compound 2 and linuron; compound 4 and linuron; compound 8 and linuron; compound 12 and linuron; compound 2 and MCPA; compound 4 and MCPA; compound 8 and MCPA; compound 12 and MCPA; compound 2 and MCPA-isoctyl; compound 4 and MCPA-isoctyl; compound 8 and MCPA-isoctyl; compound 12 and MCPA-isoctyl; compound 2 and MCPA-thioethyl; compound 4 and MCPA-thioethyl; compound 8 and MCPA-thioethyl; compound 12 and MCPA-thioethyl; compound 2 and mesosulfuron-methyl; compound 4 and mesosulfuron-methyl; compound 8 and mesosulfuron-methyl; compound 12 and mesosulfuron-methyl; compound 2 and S-metolachlor; compound 4 and S-metolachlor; compound 8 and S-metolachlor; compound 12 and S-metolachlor; compound 2 and metribuzin; compound 4 and metribuzin; compound 8 and metribuzin; compound 12 and metribuzin; compound 2 and metsulfuron-methyl; compound 4 and metsulfuron-methyl; compound 8 and metsulfuron-methyl; compound 12 and metsulfuron-methyl; compound 2 and nicosulfuron; compound 4 and nicosulfuron; compound 8 and nicosulfuron; compound 12 and nicosulfuron; compound 2 and oxyfluorfen; compound 4 and oxyfluorfen; compound 8 and oxyfluorfen; compound 12 and oxyfluorfen; compound 2 and pendimethalin; compound 4 and pendimethalin; compound 8 and pendimethalin; compound 12 and pendimethalin; compound 2 and pinoxaden; compound 4 and pinoxaden; compound 8 and pinoxaden; compound 12 and pinoxaden; compound 2 and pronamide; compound 4 and pronamide; compound 8 and pronamide; compound 12 and pronamide; compound 2 and prosulfuron; compound 4 and prosulfuron; compound 8 and prosulfuron; compound 12 and prosulfuron; compound 2 and pyroxasulfone; compound 4 and pyroxasulfone; compound 8 and pyroxasulfone; compound 12 and pyroxasulfone; compound 2 and pyroxsulam; compound 4 and pyroxsulam; compound 8 and pyroxsulam; compound 12 and pyroxsulam; compound 2 and quinclorac; compound 4 and quinclorac; compound 8 and quinclorac; compound 12 and quinclorac; compound 2 and rimsulfuron; compound 4 and rimsulfuron; compound 8 and rimsulfuron; compound 12 and rimsulfuron; compound 2 and saflufenacil; compound 4 and saflufenacil; compound 8 and saflufenacil; compound 12 and saflufenacil; compound 2 and sulfentrazone; compound 4 and sulfentrazone; compound 8 and sulfentrazone; compound 12 and sulfentrazone; compound 2 and thifensulfuron-methyl; compound 4 and thifensulfuron-methyl; compound 8 and thifensulfuron-methyl; compound 12 and thifensulfuron-methyl; compound 2 and triasulfuron; compound 4 and triasulfuron; compound 8 and triasulfuron; compound 12 and triasulfuron; compound 2 and tribenuron-methyl; compound 4 and tribenuron-methyl; compound 8 and tribenuron-methyl; compound 12 and tribenuron-methyl; compound 2 and triclopyr; compound 4 and triclopyr; compound 8 and triclopyr; compound 12 and triclopyr; compound 2 and triclopyr-butotyl; compound 4 and triclopyr-butotyl; compound 8 and triclopyr-butotyl; compound 12 and triclopyr-butotyl; compound 2 and triclopyr-triethylammonium; compound 4 and triclopyr-triethylammonium; compound 8 and triclopyr-triethylammonium; compound 12 and triclopyr-triethylammonium.

Table A1 lists specific combinations of a compound of Formula 1 (i.e. Component (a)) with an additional active ingredient (i.e. Component (b)) illustrative of the mixtures, compositions and methods of the present invention. The first column of Table A1 lists compound 45 as the illustrative compound of Formula 1. The second column of Table A1 lists the specific Component (b) compound (e.g., “2,4-D” in the first line). The third, fourth and fifth columns of Table A1 lists ranges of weight ratios for rates at which the Component (b) compound is typically applied to a field-grown crop relative to Component (a). Thus, for example, the first line of Table A1 specifically discloses the combination of Component (a) with 2,4-D is typically applied in a weight ratio between 1:192 to 6:1. The remaining lines of Table A1 are to be construed similarly.

TABLE A1 More Most Typical Typical Typical Weight Weight Weight Component (a) Component (b) Ratio Ratio Ratio Compound 47 2,4-D 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 47 acetochlor 1:768 to 2:1 1:256 to 1:2 1:96 to 1:11 Compound 47 acifluorfen 1:96 to 12:1 1:32 to 4:1 1:12 to 1:2 Compound 47 aclonifen 1:857 to 2:1 1:285 to 1:3 1:107 to 1:12 Compound 47 alachlor 1:768 to 2:1 1:256 to 1:2 1:96 to 1:11 Compound 47 ametryn 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 amicarbazone 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 47 amidosulfuron 1:6 to 168:1 1:2 to 56:1 1:1 to 11:1 Compound 47 amino- 1:48 to 24:1 1:16 to 8:1 1:6 to 2:1 cyclopyrachlor Compound 47 aminopyralid 1:20 to 56:1 1:6 to 19:1 1:2 to 4:1 Compound 47 amitrole 1:768 to 2:1 1:256 to 1:2 1:96 to 1:11 Compound 47 anilofos 1:96 to 12:1 1:32 to 4:1 1:12 to 1:2 Compound 47 asulam 1:960 to 2:1 1:320 to 1:3 1:120 to 1:14 Compound 47 atrazine 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 47 azimsulfuron 1:6 to 168:1 1:2 to 56:1 1:1 to 11:1 Compound 47 beflubutamid 1:342 to 4:1 1:114 to 2:1 1:42 to 1:5 Compound 47 benfuresate 1:617 to 2:1 1:205 to 1:2 1:77 to 1:9 Compound 47 bensulfuron 1:25 to 45:1 1:8 to 15:1 1:3 to 3:1 Compound 47 bentazon 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 47 benzobicyclon 1:85 to 14:1 1:28 to 5:1 1:10 to 1:2 Compound 47 benzofenap 1:257 to 5:1 1:85 to 2:1 1:32 to 1:4 Compound 47 bicyclopyrone 1:42 to 27:1 1:14 to 9:1 1:5 to 2:1 Compound 47 bifenox 1:257 to 5:1 1:85 to 2:1 1:32 to 1:4 Compound 47 bispyribac- 1:10 to 112:1 1:3 to 38:1 1:1 to 7:1 sodium Compound 47 bromacil 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 bromobutide 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 bromoxynil 1:96 to 12:1 1:32 to 4:1 1:12 to 1:2 Compound 47 butachlor 1:768 to 2:1 1:256 to 1:2 1:96 to 1:11 Compound 47 butafenacil 1:42 to 27:1 1:14 to 9:1 1:5 to 2:1 Compound 47 butylate 1:1542 to 1:2 1:514 to 1:5 1:192 to 1:22 Compound 47 carfenstrole 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 47 carfentrazone 1:128 to 9:1 1:42 to 3:1 1:16 to 1:2 Compound 47 chlorimuron 1:8 to 135:1 1:2 to 45:1 1:1 to 9:1 Compound 47 chlorotoluron 1:768 to 2:1 1:256 to 1:2 1:96 to 1:11 Compound 47 chlorsulfuron 1:6 to 168:1 1:2 to 56:1 1:1 to 11:1 Compound 47 cincosulfuron 1:17 to 68:1 1:5 to 23:1 1:2 to 5:1 Compound 47 cinidon-ethyl 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 cinmethylin 1:34 to 34:1 1:11 to 12:1 1:4 to 3:1 Compound 47 clethodim 1:48 to 24:1 1:16 to 8:1 1:6 to 2:1 Compound 47 clodinafop 1:20 to 56:1 1:6 to 19:1 1:2 to 4:1 Compound 47 clomazone 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 clomeprop 1:171 to 7:1 1:57 to 3:1 1:21 to 1:3 Compound 47 clopyralid 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 47 cloransulam 1:12 to 96:1 1:4 to 32:1 1:1 to 6:1 Compound 47 cumyluron 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 cyanazine 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 cyclosul- 1:17 to 68:1 1:5 to 23:1 1:2 to 5:1 famuron Compound 47 cycloxydim 1:96 to 12:1 1:32 to 4:1 1:12 to 1:2 Compound 47 cyhalofop 1:25 to 45:1 1:8 to 15:1 1:3 to 3:1 Compound 47 daimuron 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 47 desmedipham 1:322 to 4:1 1:107 to 2:1 1:40 to 1:5 Compound 47 dicamba 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 47 dichlobenil 1:1371 to 1:2 1:457 to 1:4 1:171 to 1:20 Compound 47 dichlorprop 1:925 to 2:1 1:308 to 1:3 1:115 to 1:13 Compound 47 diclofop 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 diclosulam 1:10 to 112:1 1:3 to 38:1 1:1 to 7:1 Compound 47 difenzoquat 1:288 to 4:1 1:96 to 2:1 1:36 to 1:4 Compound 47 diflufenican 1:857 to 2:1 1:285 to 1:3 1:107 to 1:12 Compound 47 diflufenzopyr 1:12 to 96:1 1:4 to 32:1 1:1 to 6:1 Compound 47 dimethachlor 1:768 to 2:1 1:256 to 1:2 1:96 to 1:11 Compound 47 dimethametryn 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 47 dimethenamid 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 dithiopyr 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 47 diuron 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 EPTC 1:768 to 2:1 1:256 to 1:2 1:96 to 1:11 Compound 47 esprocarb 1:1371 to 1:2 1:457 to 1:4 1:171 to 1:20 Compound 47 ethalfluralin 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 ethametsulfuron 1:17 to 68:1 1:5 to 23:1 1:2 to 5:1 Compound 47 ethoxyfen 1:8 to 135:1 1:2 to 45:1 1:1 to 9:1 Compound 47 ethoxysulfuron 1:20 to 56:1 1:6 to 19:1 1:2 to 4:1 Compound 47 etobenzanid 1:257 to 5:1 1:85 to 2:1 1:32 to 1:4 Compound 47 fenoxaprop 1:120 to 10:1 1:40 to 4:1 1:15 to 1:2 Compound 47 fenoxasulfone 1:85 to 14:1 1:28 to 5:1 1:10 to 1:2 Compound 47 fentrazamide 1:17 to 68:1 1:5 to 23:1 1:2 to 5:1 Compound 47 flazasulfuron 1:17 to 68:1 1:5 to 23:1 1:2 to 5:1 Compound 47 florasulam 1:2 to 420:1 1:1 to 140:1 2:1 to 27:1 Compound 47 fluazifop 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 47 flucarbazone 1:8 to 135:1 1:2 to 45:1 1:1 to 9:1 Compound 47 flucetosulfuron 1:8 to 135:1 1:2 to 45:1 1:1 to 9:1 Compound 47 flufenacet 1:257 to 5:1 1:85 to 2:1 1:32 to 1:4 Compound 47 flumetsulam 1:24 to 48:1 1:8 to 16:1 1:3 to 3:1 Compound 47 flumiclorac 1:10 to 112:1 1:3 to 38:1 1:1 to 7:1 Compound 47 flumioxazin 1:25 to 45:1 1:8 to 15:1 1:3 to 3:1 Compound 47 fluometuron 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 flupyrsulfuron 1:3 to 336:1 1:1 to 112:1 2:1 to 21:1 Compound 47 fluridone 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 fluroxypyr 1:96 to 12:1 1:32 to 4:1 1:12 to 1:2 Compound 47 flurtamone 1:857 to 2:1 1:285 to 1:3 1:107 to 1:12 Compound 47 fomesafen 1:96 to 12:1 1:32 to 4:1 1:12 to 1:2 Compound 47 foramsulfuron 1:13 to 84:1 1:4 to 28:1 1:1 to 6:1 Compound 47 glufosinate 1:288 to 4:1 1:96 to 2:1 1:36 to 1:4 Compound 47 glyphosate 1:288 to 4:1 1:96 to 2:1 1:36 to 1:4 Compound 47 halosulfuron 1:17 to 68:1 1:5 to 23:1 1:2 to 5:1 Compound 47 haloxyfop 1:34 to 34:1 1:11 to 12:1 1:4 to 3:1 Compound 47 hexazinone 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 47 imazamox 1:13 to 84:1 1:4 to 28:1 1:1 to 6:1 Compound 47 imazapic 1:20 to 56:1 1:6 to 19:1 1:2 to 4:1 Compound 47 imazapyr 1:85 to 14:1 1:28 to 5:1 1:10 to 1:2 Compound 47 imazaquin 1:34 to 34:1 1:11 to 12:1 1:4 to 3:1 Compound 47 imazethabenz 1:171 to 7:1 1:57 to 3:1 1:21 to 1:3 Compound 47 imazethapyr 1:24 to 48:1 1:8 to 16:1 1:3 to 3:1 Compound 47 imazosulfuron 1:27 to 42:1 1:9 to 14:1 1:3 to 3:1 Compound 47 indanofan 1:342 to 4:1 1:114 to 2:1 1:42 to 1:5 Compound 47 indaziflam 1:25 to 45:1 1:8 to 15:1 1:3 to 3:1 Compound 47 iodosulfuron 1:3 to 336:1 1:1 to 112:1 2:1 to 21:1 Compound 47 ioxynil 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 47 ipfencarbazone 1:85 to 14:1 1:28 to 5:1 1:10 to 1:2 Compound 47 isoproturon 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 isoxaben 1:288 to 4:1 1:96 to 2:1 1:36 to 1:4 Compound 47 isoxaflutole 1:60 to 20:1 1:20 to 7:1 1:7 to 2:1 Compound 47 lactofen 1:42 to 27:1 1:14 to 9:1 1:5 to 2:1 Compound 47 lenacil 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 linuron 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 MCPA 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 47 MCPB 1:288 to 4:1 1:96 to 2:1 1:36 to 1:4 Compound 47 mecoprop 1:768 to 2:1 1:256 to 1:2 1:96 to 1:11 Compound 47 mefenacet 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 mefluidide 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 47 mesosulfuron 1:5 to 224:1 1:1 to 75:1 1:1 to 14:1 Compound 47 mesotrione 1:42 to 27:1 1:14 to 9:1 1:5 to 2:1 Compound 47 metamifop 1:42 to 27:1 1:14 to 9:1 1:5 to 2:1 Compound 47 metazachlor 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 metazosulfuron 1:25 to 45:1 1:8 to 15:1 1:3 to 3:1 Compound 47 metha- 1:768 to 2:1 1:256 to 1:2 1:96 to 1:11 benzthiazuron Compound 47 metolachlor 1:768 to 2:1 1:256 to 1:2 1:96 to 1:11 Compound 47 metosulam 1:8 to 135:1 1:2 to 45:1 1:1 to 9:1 Compound 47 metribuzin 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 47 metsulfuron 1:2 to 560:1 1:1 to 187:1 3:1 to 35:1 Compound 47 molinate 1:1028 to 2:1 1:342 to 1:3 1:128 to 1:15 Compound 47 napropamide 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 naptalam 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 47 nicosulfuron 1:12 to 96:1 1:4 to 32:1 1:1 to 6:1 Compound 47 norflurazon 1:1152 to 1:1 1:384 to 1:3 1:144 to 1:16 Compound 47 orbencarb 1:1371 to 1:2 1:457 to 1:4 1:171 to 1:20 Compound 47 ortho- 1:20 to 56:1 1:6 to 19:1 1:2 to 4:1 sulfamuron Compound 47 oryzalin 1:514 to 3:1 1:171 to 1:2 1:64 to 1:8 Compound 47 oxadiargyl 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 oxadiazon 1:548 to 3:1 1:182 to 1:2 1:68 to 1:8 Compound 47 oxasulfuron 1:27 to 42:1 1:9 to 14:1 1:3 to 3:1 Compound 47 oxaziclomefone 1:42 to 27:1 1:14 to 9:1 1:5 to 2:1 Compound 47 oxyfluorfen 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 paraquat 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 47 pendimethalin 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 penoxsulam 1:10 to 112:1 1:3 to 38:1 1:1 to 7:1 Compound 47 penthoxamid 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 pentoxazone 1:102 to 12:1 1:34 to 4:1 1:12 to 1:2 Compound 47 phenmedipham 1:102 to 12:1 1:34 to 4:1 1:12 to 1:2 Compound 47 picloram 1:96 to 12:1 1:32 to 4:1 1:12 to 1:2 Compound 47 picolinafen 1:34 to 34:1 1:11 to 12:1 1:4 to 3:1 Compound 47 pinoxaden 1:25 to 45:1 1:8 to 15:1 1:3 to 3:1 Compound 47 pretilachlor 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 47 primisulfuron 1:8 to 135:1 1:2 to 45:1 1:1 to 9:1 Compound 47 prodiamine 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 profoxydim 1:42 to 27:1 1:14 to 9:1 1:5 to 2:1 Compound 47 prometryn 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 propachlor 1:1152 to 1:1 1:384 to 1:3 1:144 to 1:16 Compound 47 propanil 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 propaquizafop 1:48 to 24:1 1:16 to 8:1 1:6 to 2:1 Compound 47 propoxy- 1:17 to 68:1 1:5 to 23:1 1:2 to 5:1 carbazone Compound 47 propyrisulfuron 1:17 to 68:1 1:5 to 23:1 1:2 to 5:1 Compound 47 propyzamide 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 prosulfocarb 1:1200 to 1:2 1:400 to 1:4 1:150 to 1:17 Compound 47 prosulfuron 1:6 to 168:1 1:2 to 56:1 1:1 to 11:1 Compound 47 pyraclonil 1:42 to 27:1 1:14 to 9:1 1:5 to 2:1 Compound 47 pyraflufen 1:5 to 224:1 1:1 to 75:1 1:1 to 14:1 Compound 47 pyrasulfotole 1:13 to 84:1 1:4 to 28:1 1:1 to 6:1 Compound 47 pyrazolynate 1:857 to 2:1 1:285 to 1:3 1:107 to 1:12 Compound 47 pyrazosulfuron 1:10 to 112:1 1:3 to 38:1 1:1 to 7:1 Compound 47 pyrazoxyfen 1:5 to 224:1 1:1 to 75:1 1:1 to 14:1 Compound 47 pyribenzoxim 1:10 to 112:1 1:3 to 38:1 1:1 to 7:1 Compound 47 pyributicarb 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 pyridate 1:288 to 4:1 1:96 to 2:1 1:36 to 1:4 Compound 47 pyriftalid 1:10 to 112:1 1:3 to 38:1 1:1 to 7:1 Compound 47 pyriminobac 1:20 to 56:1 1:6 to 19:1 1:2 to 4:1 Compound 47 pyrimisulfan 1:17 to 68:1 1:5 to 23:1 1:2 to 5:1 Compound 47 pyrithiobac 1:24 to 48:1 1:8 to 16:1 1:3 to 3:1 Compound 47 pyroxasulfone 1:85 to 14:1 1:28 to 5:1 1:10 to 1:2 Compound 47 pyroxsulam 1:5 to 224:1 1:1 to 75:1 1:1 to 14:1 Compound 47 quinclorac 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 47 quizalofop 1:42 to 27:1 1:14 to 9:1 1:5 to 2:1 Compound 47 rimsulfuron 1:13 to 84:1 1:4 to 28:1 1:1 to 6:1 Compound 47 saflufenacil 1:25 to 45:1 1:8 to 15:1 1:3 to 3:1 Compound 47 sethoxydim 1:96 to 12:1 1:32 to 4:1 1:12 to 1:2 Compound 47 simazine 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 sulcotrione 1:120 to 10:1 1:40 to 4:1 1:15 to 1:2 Compound 47 sulfentrazone 1:147 to 8:1 1:49 to 3:1 1:18 to 1:3 Compound 47 sulfometuron 1:34 to 34:1 1:11 to 12:1 1:4 to 3:1 Compound 47 sulfosulfuron 1:8 to 135:1 1:2 to 45:1 1:1 to 9:1 Compound 47 tebuthiuron 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 tefuryltrione 1:42 to 27:1 1:14 to 9:1 1:5 to 2:1 Compound 47 tembotrione 1:31 to 37:1 1:10 to 13:1 1:3 to 3:1 Compound 47 tepraloxydim 1:25 to 45:1 1:8 to 15:1 1:3 to 3:1 Compound 47 terbacil 1:288 to 4:1 1:96 to 2:1 1:36 to 1:4 Compound 47 terbuthyl- 1:857 to 2:1 1:285 to 1:3 1:107 to atrazine 1:12 Compound 47 terbutryn 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 47 thenylchlor 1:85 to 14:1 1:28 to 5:1 1:10 to 1:2 Compound 47 thiazopyr 1:384 to 3:1 1:128 to 1:1 1:48 to 1:6 Compound 47 thiencarbazone 1:3 to 336:1 1:1 to 112:1 2:1 to 21:1 Compound 47 thifensulfuron 1:5 to 224:1 1:1 to 75:1 1:1 to 14:1 Compound 47 thiobencarb 1:768 to 2:1 1:256 to 1:2 1:96 to 1:11 Compound 47 topramazone 1:6 to 168:1 1:2 to 56:1 1:1 to 11:1 Compound 47 tralkoxydim 1:68 to 17:1 1:22 to 6:1 1:8 to 2:1 Compound 47 triallate 1:768 to 2:1 1:256 to 1:2 1:96 to 1:11 Compound 47 triasulfuron 1:5 to 224:1 1:1 to 75:1 1:1 to 14:1 Compound 47 triaziflam 1:171 to 7:1 1:57 to 3:1 1:21 to 1:3 Compound 47 tribenuron 1:3 to 336:1 1:1 to 112:1 2:1 to 21:1 Compound 47 triclopyr 1:192 to 6:1 1:64 to 2:1 1:24 to 1:3 Compound 47 trifloxysulfuron 1:2 to 420:1 1:1 to 140:1 2:1 to 27:1 Compound 47 trifluralin 1:288 to 4:1 1:96 to 2:1 1:36 to 1:4 Compound 47 triflusulfuron 1:17 to 68:1 1:5 to 23:1 1:2 to 5:1 Compound 47 tritosulfuron 1:13 to 84:1 1:4 to 28:1 1:1 to 6:1

The present disclosure also includes Tables A2 through A22 which are each constructed the same as Table A1 above except that entries below the “Component (a)” column heading are replaced with the respective Component (a) Column Entry shown below. Thus, for example, in Table A2 the entries below the “Component (a)” column heading all recite “Compound 50”, and the first line below the column headings in Table A2 specifically discloses a mixture of Compound 50 with 2,4-D. Tables A3 through A22 are constructed similarly.

Table Number Component (a) Column Entries A2 Compound 50 A3 Compound 52 A4 Compound 59 A5 Compound 75 A6 Compound 81 A7 Compound 82 A8 Compound 83 A9 Compound 85 A10 Compound 87 A11 Compound 96 A12 Compound 97 A13 Compound 107 A14 Compound 118 A15 Compound 128 A16 Compound 133 A17 Compound 169 A18 Compound 175 A19 Compound 186 A20 Compound 218 A21 Compound 240 A22 Compound 243

The following Tests demonstrate the herbicidal effect of the compounds of this invention against specific weeds. The weed control afforded by the compounds is not limited, however, to the plant species tested. See Index Tables A-I for compound descriptions. The following abbreviations are used in the Index Tables which follow: “Cmpd” means Compound, Me is methyl, Et is ethyl, c-Pr is cyclopropyl, i-Bu is isobutyl (i.e. —CH₂CH(CH₃)₂), Ph is phenyl, OMe is methoxy, c-hex is cyclohexyl, n-hex is normal hexyl Bn in benzyl, acetylene means —C≡CH, and SMe is methylthio. The abbreviation “Ex.” stands for “Example” and is followed by a number indicating in which example the compound is prepared. Substitution is noted in parentheses following the listed ring, for example Ph(4-OMe) indicates that the phenyl group is substituted by methoxy at the 4-position (relative to the point of attachment of the phenyl group to the remainder of the Formula 1 compound).

INDEX TABLE A

Cmpd R¹ R² R³ m.p.(° C.)  1 CH₃ c-Pr OH *  2 (Ex. 1) Ph Ph OH * **  3 Et c-Pr OH *  4 Ph(4-OMe) Ph OH *  7 Ph Et OH *  8 Ph(4-Me) Ph OH *  9 Ph(3-Cl) Ph OH 101-102  10 Ph(2-Cl) Ph OH 142-143  11 Ph(4-Cl) Ph OH 83-85  12 Ph(2-Me) Ph OH 181-182  13 Ph(4-Cl) Ph O⁻K⁺ 105-108  14 Ph Ph O⁻K⁺ 128-130  15 Ph(2-OMe) Ph OH 178-179  17 (Ex. 2) —CH₂Ph Ph OH 57-58 **  18 Ph(3-Me) Ph OH 77-78  19 Ph(3-OMe) Ph OH 87-88  22 Ph(3-F) Ph OH 72-74  23 —CH₂CH═CH₂ Ph OH 38-40  24 Ph(4-F) Ph OH 131-132  25 Ph Ph(4-Cl) OH *  26 Ph(2-F) Ph OH 142-144  27 Ph(2,3-di-Me) Ph OH 155-157  28 Ph(2,4-di-Me) Ph OH 186-187  29 Ph(2,5-di-Me) Ph OH 169-171  30 Ph SMe OH 92-94  31 Ph(2,6-di-Me) Ph OH 177-178  32 Ph(3,4-di-Me) Ph OH 165-166  33 Ph(3,5-di-Me) Ph OH 156-157  34 Ph Ph(3-Cl) OH 131-135  35 Ph Ph(2-Cl) OH 138-142  36 Ph(2-Me) Ph(3-Cl) OH 82-83  37 Ph(2-Br) Ph OH 170-171  38 Ph(3-Br) Ph OH 105-107  39 Ph(4-Me) Ph(3-Cl) OH 78-80  40 Ph(3-Cl-2-Me) Ph OH 170-171  41 Ph(2-Cl-4-Me) Ph OH 183-184  42 Ph n-Bu OH 145-147  43 Ph(4-Cl-2-Me) Ph OH 172-173  44 Ph(5-F-2-Me) Ph OH 169-170  45 Ph(3-Me) Ph(3-Cl) OH 69-70  46 Ph(2-Cl-6-Me) Ph OH 180-181  47 (Ex. 5) Ph(3-F-2-Me) Ph OH 168-169  48 Ph(4-F-2-Me) Ph OH 153-155  49 Et Ph OH 62-66  50 n-Pr Ph OH 106-108  51 Ph(2-F-5-Me) Ph OH 159-161  52 Ph(5-Cl-2-Me) Ph OH 165-166  53 Ph(4-F-3-Me) Ph OH 152-153  54 Ph n-hex OH 138-140  55 Me Ph OH 152-154  56 Ph 3-thienyl OH *  57 Ph(2,4-di-F) Ph OH 153-154  58 Ph(2-F,3-Me) Ph OH 161-162  59 —CH₂(tetrahydrofuran-2yl) Ph OH 155-156  60 Ph i-Pr OH *  61 —CH₂C≡CH Ph 151-153  62 Ph(2-Me) n-Bu OH 100-101  63 Ph(3-Me) n-Bu OH 136-137  64 Ph(4-Cl) Ph(3-Cl) OH 140-142  65 Ph 2-thienyl(5-Cl) OH *  66 Ph 2-thienyl OH *  67 Ph(4-Me) n-Bu OH 143-144  68 Ph i-Bu OH *  69 Ph Ph(3-Br) OH *  70 Ph Ph(4-Br) OH *  71 Ph Ph(2-Br) OH *  72 n-Pr n-Pr OH 95-97  73 Ph(2-Me) n-Pr OH 127-128  74 —CH₂(tetrahydrofuran-2-yl) n-Pr OH 95-96  75 n-Bu n-Pr OH 88-89  76 Ph furan-2-yl OH *  77 n-Pr 2-thienyl OH *  78 Ph n-pentyl OH *  79 Ph(3-Me) n-Pr OH 140-142  80 Ph Ph(4-Me) OH 164-169  81 —CH₂CH₂CH₂OCH₃ Ph OH 121-122  82 Ph Ph(2-Me) OH 165-167  83 Ph Ph OC(═O)-i-Bu 175-176  84 —CH₂(Ph(3,4-di-OMe)) n-Pr OH *  85 —CH₂CH₂OCH₃ Ph OH 135-137  86 n-Bu Ph OH *  87 Ph c-Pr OH *  88 Ph Ph OC(═O)-c-Pr 167-168  89 n-pentyl Ph OH 100-102  90 c-Pr Ph OH 172-174  91 —CH₂CH₂OCH₂CH₂OCH₃ Ph OH 138-139  92 Ph c-pentyl OH *  93 n-Pr 3-thienyl OH *  94 n-hex Ph OH 95-97  95 i-Pr Ph OH 163-165  96 —CH₂CH₂OCH₂CH₃ Ph OH 129-131  97 (Ex. 10) —CH₂CH₂OCH₃ 3-thienyl OH 103-105  98 —CH₂(tetrahydrofuran-2-yl) 3-thienyl OH *  99 c-hex 3-thienyl OH * 100 n-Pr Ph(3-OMe) OH * 101 n-Pr Ph(2-F) OH 136-138 102 n-Pr Ph(4-F) OH 100-103 103 Bn n-Pr OH * 104 —CH₂(Ph(3-OMe)) n-Pr OH * 105 —CH₂(Ph(3-OCF₃)) n-Pr OH * 106 Ph c-hex OH * 107 —CH(CH₃)CH₂OCH₃ Ph OH 122-123 108 —CH₂CH₂OCH₃ 2-thienyl OH * 109 —CH₂(tetrahydrofuran-2-yl) 2-thienyl OH * 110 n-Pr furan-2-yl OH * 111 —CH₂CH₂OCH₃ furan-2-yl OH * 112 n-Pr Ph(4-OMe) OH * 113 (Ex. 7) Ph 3-pyridinyl OH ** 114 Ph c-Bu OH * 115 Et Ph(3-Me) OH * 116 n-Bu Ph(3-Me) OH * 117 —CH₂CH₂OCH₃ Ph(3-Me) OH * 118 —CH₂CH₂CH₂OCH₃ Ph(3-Me) OH * 119 —CH₂CH₂OCH₃ Ph(3,5-di-F) OH 154-178 120 —CH₂CH₂CH₂OCH₃ Ph(3,5-di-F) OH 139-140 121 n-Bu Ph(3,5-di-F) OH 144-145 122 Et Ph(3,5-di-F) OH 162-165 123 —CH₂CH₂OCH₃ Ph(3-F) OH * 124 Et Ph(3-F) OH * 125 n-Bu Ph(3-F) OH * 126 —CH₂CH₂CH₂OCH₃ Ph(3-F) OH * 127 n-Pr Ph(3-F) OH * 128 (Ex. 11) c-hex Ph OH 160-163 ** 129 tetrahydropyran-4-yl Ph OH * 130 c-heptyl Ph OH * 131 c-pentyl Ph OH * 132 Ph(4-F-3-Me) Ph(3-Br) OH * 133 Ph(4-F-3-Me) Ph(3-Cl) OH * 134 n-Pr Ph(4-Br) OH * 135 n-Pr 1-Me-pyrazol-3-yl OH * 136 —CH₂CH₂OCH₃ 1-Me-pyrazol-3-yl OH * 137 Et Ph(3-Br) OH 141-145 138 n-Bu Ph(3-Br) OH 112-113 139 —CH₂CH₂OCH₃ Ph(3-Br) OH 115-116 140 —CH₂CH₂CH₂OCH₃ Ph(3-Br) OH 118-119 141 n-Pr Ph(3-Br) OH 134-137 142 —CH₂(tetrahydrofuran-2-yl) Ph(3-Cl) OH * 143 —CH₂CH₂CH₂OCH₃ Ph(3-Cl) OH * 144 Ph(5-Cl-2-Me) Ph(3-Br) OH * 145 Et Ph(3-Cl) OH 114-115 146 n-Bu Ph(3-Cl) OH 104-112 147 —CH₂CH₂OCH₃ Ph(3-Cl) OH 124-125 148 Ph(5-Cl-2-Me) Ph(3-Cl) OH * 149 n-Pr 1,4-benzodioxan-6-yl OH * 150 n-Pr naphthalen-2-yl OH * 151 Ph(4-OMe) Ph(3-Cl) OH 154-156 152 n-Pr Ph(3,5-di-F) OH * 153 n-Pr c-Pr OH 163-165 154 Ph(5-F-2-Me) Ph(3-Br) OH * 155 n-Pr Ph(3-CF₃) OH 129-131 156 n-Pr Ph(3,5-di-Me) OH 161-163 157 Ph(5-F-2-Me) Ph(3-Cl) OH * 158 Ph(4-Et) Ph(3,5-di-F) OH 181-182 159 Ph(2-Me) Ph(3,5-di-F) OH 166-168 160 c-hex c-Pr OH 173-175 161 Ph Ph(3,5-di-F) OH 147-148 162 Ph(4-Me) Ph(3,5-di-F) OH 191-192 163 —CH₂-c-hex Ph(3,5-di-F) OH * 164 tetrahydrothiopyran-4-yl Ph OH * 165 c-dodecahexyl Ph OH * 166 Ph(4-F-2-Me) Ph(3-Br) OH * 167 Ph(4-F-2-Me) Ph(3-Cl) OH * 168 (Ex. 8) (cis/trans)-tetrahydro-1-oxido-2H- Ph OH ** thiopyran-4-yl 169 (Ex. 8) (trans/cis)-tetrahydro-1-oxido-2H- Ph OH ** thiopyran-4-yl 170 —CH₂C≡CH Ph(3,5-di-F) OH * 171 —CH₂CH₂OCH₂CH₂OCH₃ Ph(3,5-di-F) OH * 172 n-Pr Ph(3-Me) OH 116-117 173 n-Pr Ph(3,5-di-Cl) OH  97-100 174 Ph(4-Et) Ph(3-Cl) OH 146-148 175 Ph(4-Et) Ph(3-Br) OH 126-129 176 Ph(4-OMe) Ph(3-Br) OH 120-124 177 Ph(4-Et) Ph(3-Br) OH 139-142 178 Ph(5-F-2-Me) Ph(3-Me) OH * 179 Ph(5-Cl-2-Me) Ph(3,5-di-F) OH * 180 —CH₂(tetrahydrofuran-2-yl) Ph(3,5-di-F) OH * 181 c-hex Ph(3,5-di-F) OH * 182 —CH₂CH₂OCH₂CH₃ Ph(3,5-di-F) OH * 183 Ph(5-F-2-Me) Ph(3,5-di-F) OH * 184 Ph(5-Cl-2-Me) Ph(3-F) OH * 185 c-hex Ph(3-Me) OH * 186 tetrahydropyran-4-yl 3-thienyl OH * 187 c-hex Ph(3-F) OH * 188 c-hex furan-2-yl OH * 189 c-hex 2-thienyl OH * 190 n-Pr Ph(3-Cl) OH 123-125 191 Ph(4-F-3-Me) Ph(3-F) OH * 192 Ph(4-F-2-Me) Ph(3-Me) OH * 193 n-Bu c-Pr OH 140-142 194 c-hex Ph(3-Et) OH * 195 c-hex Ph(3-CF₃) OH * 196 c-hex Ph(3-OMe) OH * 197 c-hex Ph(4-F) OH * 198 c-hex Ph(3,4-di-F) OH * 199 Ph Ph(3-F) OH * 200 Et Bn OH * 201 Ph(2-Me) Ph(3-F) OH * 202 Ph(4-Me) Ph(3-F) OH * 203 Ph(4-OMe) Ph(3-F) OH * 204 Ph(4-Et) Ph(3-F) OH * 205 c-hex Ph(3,4,5-tri-F) OH * 206 c-hex Ph(3-Br) OH * 207 —CH₂CH₂CF₃ Ph OH * 208 —CH₂CH₂CF₃ Ph(3-F) OH 69-70 209 Ph(2-Me) Ph(3-Br) OH 144-146 210 Ph(2-Me) Ph(3-Me) OH 152-154 211 Ph(4-Me) Ph(3-Me) OH 146-148 212 Ph(4-OMe) Ph(3-Me) OH 156-158 213 Ph(4-Et) Ph(3-Me) OH 147-148 214 —CH₂CH₂CHCH₂ Ph OH 124-127 215 c-octyl Ph OH * 216 c-hex Ph(4-acetylene) OH * 217 Ph n-Pr OH 145-147 218 Ph(3,4-di-OMe) Ph OH 164-165 219 Ph(4-Et) Ph OH 160-162 220 Ph(3-Et) Ph OH 126-127 255 Ph(2-Et) Ph OH 171-172 256 Ph(2,4-diOMe) Ph OH 182-183 257 —CH₂CH₂CH₂CH₂CH₂— OH * *See Index Table J for M.S. or ¹H NMR data. **See synthesis examples for ¹H NMR data.

INDEX TABLE B

Cmpd R¹ R² R³ m.p. (° C.)  16 Ph Ph OS(O)₂Ph(4-Me) 63-65  20 (Ex. 3) —CH₂Ph Ph OH 56-57 **  21 (Ex. 4) —CH₂Ph Ph OS(O)₂Ph(4-Me) 52-53 ** 221 n-Pr 2-thienyl OH * *See Index Table J for M.S. or ¹H NMR data. ** See synthesis example for ¹H NMR data.

INDEX TABLE C

Cmpd R¹ R² m.p. (° C.) 222 Ph(2,5-di-Me) Ph * 223 (Ex. 6) Ph Ph ** *See Index Table J for M.S. or ¹H NMR data. **See synthesis examples for ¹H NMR data.

INDEX TABLE D

Cmpd R¹ R² R³ m.p. (° C.) 224 n-Pr Ph(3,5-di-F) OH * 225 Ph Ph OH 125-127 *See Index Table J for M.S. or ¹H NMR data.

INDEX TABLE E

Cmpd R¹ R² R³ m.p.(° C.) 226 n-Pr Ph OH * 227 n-Pr 3-thienyl OH * 228 —CH₂CH₂OCH₃ 3-thienyl OH * 229 —CH₂(tetrahydrofuran- 3-thienyl OH * 2-yl) 230 n-Pr furan-2-yl OH * 231 Et Ph(3-Me) OH * 232 n-Bu Ph(3-Me) OH * 233 —CH₂CH₂OCH₃ Ph(3-Me) OH * 234 Ph(3-F-2-Me) Ph OH * 235 —CH₂CH₂OCH₃ Ph(3-F) OH * 236 Et Ph(3-F) OH * 237 n-Bu Ph(3-F) OH * 238 —CH₂CH₂CH₂OCH₃ Ph(3-F) OH * 239 Et Ph OH * 240 n-Bu Ph OH * 241 n-Pr 1,4-benzodioxan-6-yl OH * 242 n-Pr naphthalen-2-yl OH * 243 (Ex. 9) —CH₂CH₂OCH₃ Ph(3,5-di-F) OH ** 244 —CH₂CH₂CH₂OCH₃ Ph(3,5-di-F) OH * 245 n-Bu Ph(3,5-di-F) OH * 246 Ph Ph(3,5-di-F) OH 158-159 247 c-dodecahexyl Ph OH * 248 c-hex Ph OH * 249 tetrahydropyran-4-yl Ph OH * 250 —CH₂(tetrahydrofuran- Ph OH * 2-yl) 251 c-hex Ph(3,4,5-tri-F) OH * 252 c-hex Ph(3-Br) OH * 253 c-heptyl Ph OH * 254 c-hex Ph(4-acetylene) OH * *See index table J for ¹H NMR. **See synthesis example for ¹H NMR data.

INDEX TABLE F

Cmpd R¹ R² m.p. (° C.)  2Q (Ex. 1) Ph Ph **  17Q (Ex. 2) —CH₂Ph Ph **  23Q —CH₂CH═CH₂ Ph *  47Q (Ex. 5) Ph(3-F-2-Me) Ph **  59Q —CH₂(tetrahydrofuran-2yl) Ph *  61Q —CH₂C≡CH Ph *  76Q Ph 2-furanyl *  84Q —CH₂(Ph(3,4-di-OMe)) n-Pr * 105Q —CH₂(Ph(3-OCF₃)) n-Pr * 113Q (Ex. 7) Ph 3-pyridinyl ** 153Q n-Pr c-Pr * 163Q —CH₂-c-hex Ph(3,5-di-F) * 212Q Ph(4-OMe) Ph(3-Me) * 257Q —CH₂CH₂CH₂CH₂CH₂— * *See Index Table J for MS or ¹H NMR data. **See synthesis examples for ¹H NMR data.

INDEX TABLE G

Cmpd R¹ R² m.p. (° C.) 20Q (Ex. 3) —CH₂Ph Ph ** **See synthesis example for ¹H NMR data.

INDEX TABLE H

m.p. Cmpd R¹ R² (° C.)  2R (Ex. 1) Ph Ph **  17R (Ex. 2) —CH₂Ph Ph **  23R —CH₂CH═CH₂ Ph *  47R (Ex. 5) Ph(3-F-2-Me) Ph **  59R —CH₂(tetrahydrofuran-2-yl) Ph *  61R —CH₂C≡CH Ph *  76R Ph 2-furanyl *  84R —CH₂(Ph(3,4-di-OMe)) n-Pr * 105R —CH₂(Ph(3-OCF₃)) n-Pr *  97R (Ex. 10) —CH₂CH₂OCH₃ 3-thienyl ** 118R —CH₂CH₂CH₂OCH₃ Ph(3-Me) * 113R (Ex. 7) Ph 3-pyridinyl ** 135R n-Pr 1-Me-pyrazol-3-yl * 128R (Ex. 11) c-hex Ph ** 153R n-Pr c-Pr * 163R —CH₂-c-hex Ph(3,5-di-F) * 164R tetrahydrothiopyran-4-yl Ph * 186R tetrahydropyran-4-yl 3-thienyl * 212R Ph(4-OMe) Ph(3-Me) * 216R c-hex Ph(4-acetylene) * 242R n-Pr naphthalene-2-yl * 247R c-dodecahexyl Ph * 243R (Ex. 9) —CH₂CH₂OCH₃ Ph(3,5-di-F) ** 257R —CH₂CH₂CH₂CH₂CH₂— * *See Index Table J for MS or ¹H NMR data. **See synthesis examples for ¹H NMR data.

INDEX TABLE I

m.p. Cmpd R¹ R² R²³ (° C.)  2S (Ex. 1) Ph Ph Et **  17S (Ex. 2) —CH₂Ph Ph Et **  23S —CH₂CH═CH₂ Ph Et *  59S —CH₂(tetrahydrofuran- Ph Et * 2-yl)  61S —CH₂C≡CH Ph Et *  84S —CH₂(Ph(3,4-di-OMe)) n-Pr Et * 105S —CH₂(Ph(3-OCF₃)) n-Pr Et *  97S (Ex. 10) —CH₂CH₂OCH₃ 3-thienyl Et ** 118S —CH₂CH₂CH₂OCH₃ Ph(3-Me) Et * 113S (Ex. 7) Ph 3-pyridinyl Et ** 135S n-Pr 1-Me-pyrazol- Et * 3-yl 128S (Ex. 11) c-hex Ph Et ** 153S n-Pr c-Pr Me * 163S —CH₂-c-hex Ph(3,5-di-F) Et * 164S tetrahydrothiopyran-4-yl Ph Et * 186S tetrahydropyran-4-yl 3-thienyl Et * 212S Ph(4-OMe) Ph(3-Me) Et * 216S c-hex Ph(4-acetylene) Et * 242S n-Pr naphthalene-2-yl Et * 247S c-dodecahexyl Ph Et * 243S (Ex. 9) —CH₂CH₂OCH₃ Ph(3,5-di-F) Et ** 257S —CH₂CH₂CH₂CH₂CH₂— Et * *See Index Table J for MS or ¹H NMR data. **See synthesis examples for ¹H NMR data.

INDEX TABLE J Cmpd Mass spectra data^(a) or ¹H NMR data^(b)   1 289   3 303   4 417   7 339   8 401  25 421  56 393  60 353 (ESI, M + 1)  65 427  66 393  68 367 (ESI, M + 1) (500 MHz) δ 16.38 (s, 1H), 8.14 (s, 1H), 7.45 (t, 1H), 7.34 (dd, 1H), 7.32-7.23 (m, 3H), 7.10-7.05 (m,  69 3H), 7.01-6.95 (m, 1H), 2.64 (t, 2H), 2.40 (t, 2H), 1.96 (dd, 2H).  70 465  71 463 (AP, M − H)  76 377  77 359  78 381 (ESI, M + H)  84 425 (AP, M − H)  86 367  87 351 (ESI, M + H)  92 379 (ESI, M + H)  93 359  98 401  99 399 100 381 (EST, M − H) 103 δ 16.41 (s, 1H), 8.09 (s, 1H), 7.42 (m, 3H), 7.21 (m, 2H), 5.29 (s, 2H), 2.79 (m, 2H), 2.77 (m, 2H), 2.65 (m, 2H), 2.15 (m, 2H), 1.75 (m, 2H), 0.94 (t, 3H). 104 δ 16.22 (s, 1H), 8.07 (s, 1H), 7.25 (m, 1H), 6.77 (m, 3H), 5.29 (s, 2H), 3.81 (s, 3H), 2.79 (m, 2H), 2.64 (m, 2H), 2.55 (m, 2H), 2.15 (m, 2H), 1.65 (m, 2H), 0.95 (t, 3H). 105 δ 16.41 (s, 1H), 8.06 (s, 1H), 7.41 (m, 1H), 7.14 (m, 3H), 5.32 (s, 2H), 2.81 (m, 2H), 2.62 (m, 2H), 2.52 (m, 2H), 2.15 (m, 2H), 1.81 (m, 2H), 0.95 (t, 3H). 106 393 (ESI, M + H) 108 375 109 401 110 343 111 359 112 382 114 365 (ESI, M + H) 115 353 116 381 117 383 118 397 123 387 124 357 125 385 126 401 127 δ 8.09 (s, 1H), 7.55-7.46 (m, 1H), 7.33-7.20 (m, 3H), 3.94-3.83 (m, 2H), 2.74 (t, 2H), 2.51 (t, 2H), 2.08 (quin, 2H), 1.63 (sxt, 2H), 0.78 (t, 3H). 129 395 130 407 131 379 132 495 (AP, M − H) 133 453 134 431 (ESI, M + H) 135 357 136 373 142 429 143 417 144 (500 MHz) δ 16.32 (br s, 1H), 8.22 (s, 1H), 7.55 (s, 1H), 7.46 (d, 1H), 7.25-7.06 (m, 5H), 2.70 (br s, 2H), 2.46 (d, 2H), 2.14 (s, 3H), 2.08-2.00 (m, 2H) 148 469 149 411 150 403 152 389 154 497 157 453 163 443 164 411 165 477 166 495 (AP, M − H) 167 453 170 385 171 449 178 433 179 471 180 431 181 429 182 419 183 455 184 453 185 δ 16.65 (br s, 1H), 8.00 (s, 1H), 7.20-7.40 (m, 4H), 3.90-4.00 (m, 1H), 0.90-2.80 (m, 19H). 186 401 187 411 188 383 189 399 191 437 192 433 194 421 195 461 196 423 197 411 198 429 199 403 (AP, M − H) 200 353 201 417 (AP, M − H) 202 417 (AP, M − H) 203 433 (AP, M − H) 204 431 (AP, M − H) 205 447 206 471 207 405 (AP, M − H) 215 421 216 417 221 359 222 412 224 417 226 379 227 385 228 401 229 427 230 369 231 379 232 407 233 409 234 445 235 413 236 383 237 411 238 427 239 365 240 393 241 437 242 429 244 445 245 429 247 503 248 419 249 421 250 δ 16.75 (d, 1H), 8.09 (s, 1H), 7.53 (m, 2H), 7.49 (m, 3H), 4.35 (m, 3H), 3.85 (m, 1H), 3.61 (m, 1H), 3.31 (m, 1H), 3.15 (m, 1H), 2.95 (m, 1H), 2.20-1.20 (m, 9H). 251 473 252 497 253 433 254 443 257 δ 16.60 (s, 1H), 7.94 (s, 1H), 4.32 (m, 2H), 3.02 (m, 2H), 2.74 (m, 2H), 2.45 (m, 2H), 2.06 (m, 2H), 1.85 (m, 4H), 1.8 (m, 2H).  23Q δ 8.80 (s, 1H), 7.46-7.66 (m, 5H), 6.04 (m, 1H), 5.86-5.98 (m, 1H), 5.26 (m, 1H), 5.02 (m, 1H), 4.62 (m, 2H), 2.69 (m, 2H), 2.42 (m, 2H), 2.12 (m, 2H).  59Q δ 8.78 (s, 1H), 7.49-7.57 (m, 5H), 6.03 (s, 1H), 4.28-4.39 (m, 2H), 3.94 (m, 1H), 3.59 (m, 1H), 3.33 (m, 1H), 2.68 (m, 2H), 2.45 (m, 2H), 2.12 (m, 2H), 1.99 (m, 1H), 1.76 (m, 1H), 1.57-1.66 (m, 1H), 1.39 (m, 1H).  61Q δ 8.81 (s, 1H), 7.77 (m, 2H), 7.57 (m, 3H), 6.04 (s, 1H), 4.69 (m, 2H), 2.69 (m, 2H), 2.46 (m, 3H), 2.12 (m, 2H).  76Q δ 8.91 (s, 1H), 7.60 (m, 3H), 7.56 (m, 1H), 7.28 (dd, 2H), 6.35 (dd, 1H), 6.03 (s, 1H), 5.75 (d, 1H), 2.66 (t, 2H), 2.44 (m, 2H), 2.09 (m, 2H).  84Q δ 8.71 (s, 1H), 6.80 (m, 2H), 6.78 (d, 1H), 6.01 (s, 1H), 5.34 (s, 2H), 3.86 (d, 6H), 2.8 (m, 2H), 2.75 (m, 2H), 2.45 (m, 2H), 2.20 (m, 2H), 1.80 (m, 2H), 1.00 (t, 3H). 105Q δ 8.74 (s, 1H), 7.40 (m, 1H), 7.20 (m, 1H), 7.15 (m. 1H), 7.00 (s, 1H), 6.00 (s, 1H), 5.40 (s, 2H), 2.78 (m, 2H), 2.72 (m, 2H), 2.40 (m, 2H), 2.15 (m, 2H), 1.80 (m, 2H), 0.94 (m, 3H). 153Q (300 MHz) δ 8.57 (s, 1H), 5.98 (s, 1H), 4.25-4.19 (m, 2H), 2.67-2.63 (m, 2H), 2.45-2.41 (m, 2H), 2.13-1.92 (m, 3H), 1.86-1.78 (m, 2H), 1.42-1.37 (m, 2H), 1.26-1.20 (m, 2H), 1.07-1.02 (m, 3H). 163Q (500 MHz) δ 8.72 (s, 1H), 7.13-6.95 (m, 3H), 6.03 (s, 1H), 3.98 (d, 2H), 2.69 (td, 2H), 2.53-2.39 (m, 2H), 2.12 (quin, 2H), 1.75 (ddt, 1H), 1.66-1.57 (m, 3H), 1.50-1.43 (m, 2H), 1.19-0.99 (m, 3H), 0.77- 0.66 (m, 2H). 212Q δ 8.86 (s., 1H), 7.07-7.32 (m, 4H), 6.80-7.06 (m, 4H), 6.04 (s., 1H), 3.78 (s, 3H), 2.67 (m, 2H), 2.44 (m, 2H), 2.27 (s, 3H), 2.11 (m, 2H). 257Q δ 8.60 (s, 1H), 6.00 (s, 1H), 4.40 (m, 2H), 3.15 (m, 2H), 2.66 (m, 2H), 2.44 (m, 2H), 2.15 (m, 2H), 1.85 (m, 6H).  23R δ 9.03 (s, 1H), 7.42-7.76 (m, 5H), 5.82-6.04 (m, 1H), 5.42 (m, 1H), 5.04 (m, 1H), 4.72 (m, 2H).  59R δ 9.00 (s, 1H), 7.48-7.60 (m, 5H), 4.35 (m, 1H), 4.24-4.32 (m, 1H), 4.06 (m, 1H), 3.53-3.65 (m, 1H), 3.29-3.41 (m, 1H), 2.02 (m, 1H), 1.79 (m, 1H), 1.57-1.69 (m, 1H), 1.41 (m, 1H).  61R δ 13.02 (br s, 1H), 8.65 (s, 1H), 7.73 (m, 2H), 7.62 (m, 3H), 4.58 (m, 2H), 3.44 (m, 1H).  76R δ 12.64 (br s, 1H), 9.11 (s, 1H), 7.66 (m, 3H), 7.56 (d, 1H), 7.33 (m, 2H), 6.39 (dd, 1H), 5.93 (d, 1H).  84R δ 13.00 (br s, 1H), 8.92 (s, 1H), 6.80 (d, 1H), 6.79 (s, 1H), 6.85 (d, 1H), 5.34 (s, 2H), 3.87 (d, 6H), 2.80 (m, 2H), 1.80 (m, 2H), 1.01 (t, 3H). 105R δ 12.8 (br s, 1H), 8.94 (s, 1H), 7.45 (m, 1H), 7.25 (m, 1H), 7.15 (m, 1H), 7.05 (s, 1H), 5.41 (s, 2H), 2.77 (m, 2H), 1.88 (m, 2H), 0.99 (t, 3H). 118R δ 8.98 (s, 1H), 7.42 (m, 2H), 7.33 (m, 2H), 4.26 (m, 2H), 3.31 (t, 3H), 3.16 (s, 3H), 2.45 (s, 3H), 1.95 (m, 3H). 135R δ 13.33 (s, 1H), 8.95 (s, 1H), 7.50 (d, 1H), 7.11 (d, 1H), 4.69 (m, 2H), 4.04 (s, 3H), 1.86 (m, 2H), 1.01 (t, 3H). 153R (300 MHz) δ 13.15 (br s, 1H), 8.76 (s, 1H), 4.31-4.25 (m, 2H), 2.04-1.99 (m, 1H), 1.90-1.80 (m, 2H), 1.45-1.41 (m, 2H), 1.31-1.25 (m, 2H), 1.09 (t, 3H). 163R (500 MHz) δ 12.77 (br s, 1H), 7.19-6.94 (m, 3H), 4.08 (d, 2H), 1.86-1.52 9m, 4H), 1.44 (d, 2H), 1.22- 0.95 (m, 3H), 0.82-0.63 (m, 2H). 164R δ 13.12 (br s, 1H), 8.95 (s, 1H), 7.59 (m, 3H), 7.46 (m, 2H), 4.09 (s, 1H), 3.08 (d, 2H), 2.69 (d, 2H), 2.46 (m, 2H), 2.05 (m, 2H). 186R δ 13.12 (br s, 1H), 8.93 (s, 1H), 7.83 (m, 1H), 7.58 (m, 1H), 7.29 (m, 1H), 4.56 (m, 1H), 4.09 (m, 2H), 3.26 (m, 2H), 3.12 (m, 2H), 1.67 (m, 2H). 212R δ 9.09 (s, 1H), 6.98-7.21 (m, 6H), 6.90 (d, 2H), 3.81 (s, 3H), 2.28 (s, 3H). 216R δ 13.25 (br s, 1H), 8.93 (s, 1H), 7.67 (m, 2H), 7.48 (m, 2H), 4.06 (m, 1H), 3.28 (s, 1H), 2.68 (dd, 2H), 1.85 (d, 2H), 1.73 (d, 2H), 1.63 (m, 1H), 1.24 (m, 1H), 1.05 (m, 2H). 242R δ 13.14 (br s, 1H), 9.03 (s, 1H), 8.05 (m, 2H), 7.96 (d, 2H), 7.65 (ddd, 2H), 7.56 (dd, 1H), 4.14 (m, 2H), 1.75 (m, 2H), 0.80 (t, 3H). 247R δ 13.26 (br s, 1H), 8.96 (s, 1H), 7.57 (m, 3H), 7.46 (m, 2H), 4.45 (m, 1H), 2.32 (m, 2H), 1.99 (m, 2H), 1.18 (m, 15H), 0.69 (m, 3H). 257R δ 13.00 (br s, 1H), 8.75 (s, 1H), 4.42 (m, 2H), 3.10 (m, 2H), 1.82 (m, 6H)  23S δ 8.70 (s, 1H), 7.49-7.53 (m, 5H), 5.85-5.97 (m, 1H), 5.25 (m, 1H), 4.95 (m, 1H), 4.59 (m, 2H), 4.41 (m, 2H), 1.40 (m, 3H).  59S δ 8.68 (s, 1H), 7.46-7.55 (m, 5H), 4.40 (m, 2H), 4.28-4.35 (m, 2H), 3.88 (m, 1H), 3.58 (m, 1H), 3.31 (m, 1H), 1.91-2.02 (m, 1H), 1.52-1.81 (m, 4H), 1.39 (m, 3H).  61S δ 8.72 (s, 1H), 7.76 (m, 2H), 7.55 (m, 3H), 4.66 (m, 2H), 4.42 (m, 2H), 2.41 (s, 1H), 1.42 (m, 3H).  84S δ 8.62 (s, 1H), 6.81 (m, 2H), 6.70 (m, 1H), 5.29 (s, 2H), 4.39 (q, 2H), 3.86 (d, 6H), 2.76 (t, 2H), 1.73 (m, 2H), 1.40 (t, 3H), 0.98 (t, 3H). 105S δ 8.64 (s, 1H), 7.42 (m, 1H), 7.20 (m, 1H), 7.18 (m, 1H), 7.00 (s, 1H), 5.34 (s, 2H), 4.39 (m, 2H), 2.65 (m, 2H), 1.75 (m, 2H), 1.40 (m, 3H), 0.95 (t, 3H). 118S δ 8.66 (s, 1H), 7.38 (m, 2H), 7.29 (m, 2H), 4.40 (m, 2H), 4.11 (m, 2H), 3.30 (t, 2H), 3.15 (s, 3H), 2.43 (s, 3H), 1.93 (m, 2H), 1.40 (t, 3H). 135S δ 8.68 (s, 1H), 7.47 (d, 1H), 6.98 (d, 1H), 4.53 (m, 2H), 4.39 (q, 2H), 4.02 (s, 3H), 1.82 (m, 2H), 1.39 (t, 3H), 0.96 (t, 3H). 153S (300 MHz) δ 8.51 (s, 1H), 4.23-4.18 (m, 2H), 3.88 (s, 3H), 1.99-1.95 (m, 1H), 1.85-1.77 (m, 2H), 1.36-1.32 (m, 2H), 1.21-1.17 (m, 2H), 1.03 (t, 3H). 163S (500 MHz) δ 8.62 (s, 1H), 7.06-6.98 (m, 3H), 4.40 (q, 2H), 3.95 (d, 2H), 1.80-1.70 (m, 1H), 1.66-1.55 (m, 3H), 1.46 (d, 2H), 1.40 (t, 3H), 1.17-0.96 (m, 3H), 0.70 (dd, 2H). 164S δ 8.59 (s, 1H), 7.55 (m, 3H), 7.42 (m, 2H), 4.40 (q, 2H), 3.92 (m, 1H), 3.10 (d, 2H), 2.64 (d, 2H), 2.41 (m, 2H), 1.98 (m, 2H), 1.40 (t, 3H). 186S δ 8.57 (s, 1H), 7.71 (m, 1H), 7.52 (m, 1H), 7.24 (m, 1H), 4.39 (m, 3H), 4.04 (d, 2H), 3.17 (m, 4H), 1.58 (m, 3H), 1.39 (t, 3H). 212S δ 8.80 (s, 1H), 7.14-7.25 (m, 1H), 6.95-7.18 (m, 5 H), 6.82-6.92 (m, 2H), 3.94 (s, 3H), 3.78 (s, 3H), 2.26 (s, 3H). 216S δ 8.57 (s, 1H), 7.64 (m, 2H), 7.43 (m, 2H), 4.40 (q, 2H), 3.89 (m, 1H), 3.24 (s, 1H), 2.75 (dd, 2H), 1.78 (d, 2H), 1.63 (m, 3H), 1.55 (d, 1H), 1.39 (t, 3H), 0.99 (m, 2H). 242S δ 8.71 (s, 1H), 7.99 (m, 2H), 7.93 (d, 2H), 7.62 (m, 2H), 7.53 (dd, 1H), 4.42 (q, 2H), 4.01 (m, 2H), 1.71 (m, 2H), 1.42 (t, 3H), 0.75 (t, 3H). 247S δ 8.60 (s, 1H), 7.51 (m, 3H), 7.42 (m, 2H), 4.39 (q, 2H), 4.12 (m, 1H), 2.32 (m, 2H), 1.98 (m, 2H), 1.39 (t, 3H), 1.18 (m, 12H), 1.02 (m, 3H), 0.66 (m, 3H). 257S δ 8.47 (s, 1H), 4.34 (m, 4H), 3.02 (m, 2H), 1.82 (m, 6H), 1.36 (m, 3H). ^(a)Mass spectra are reported as the molecular weight of the highest isotopic abundance parent ion (M + 1) formed by addition of H⁺ (molecular weight of 1) to the molecule, observed by mass spectrometry using atmospheric pressure chemical ionization (AP⁺) unless otherwise noted. ^(b1)H NMR data are reported in CDCl₃ at 400 MHz unless otherwise noted; s means singlet, br s means broad singlet, d means doublet, dd means doublet of doublet, ddd means doublet of double of doublets, ddt means doublet of doublet of triplets, t means triplet, td means triplet of doublets, q means quartet, quin means quintet and sxt means sextet.

Biological Examples of the Invention Test A

Seeds of barnyardgrass (Echinochloa crus-galli), large crabgrass (Digitaria sanguinalis), giant foxtail (Setaria faberii), morningglory (Ipomoea spp.), pigweed (Amaranthus retroflexus), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum) and corn (Zea mays) were planted into a blend of loam soil and sand and treated preemergence with a directed soil spray using test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. At the same time these species were also treated with postemergence applications of test compounds formulated in the same manner.

Plants ranged in height from two to ten cm and were in the one- to two-leaf stage for the postemergence treatment. Treated plants and untreated controls were maintained in a greenhouse for approximately ten days, after which time all treated plants were compared to untreated controls and visually evaluated for injury. Plant response ratings, summarized in Table A, are based on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (-) response means no test result.

TABLE A Postemergence 1000 g ai/ha 500 g ai/ha Compound Compounds 217 1 2 3 4 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 Barnyardgrass 90 60 100 90 100 70 100 100 90 100 90 90 80 40 60 70 90 70 10 10 70 60 70 90 80 90 90 Corn 40 0 90 10 50 40 50 70 90 20 80 50 20 10 20 10 20 10 10 0 40 0 30 20 20 30 0 Crabgrass, Large 100 80 100 90 90 70 90 90 100 90 100 90 90 70 40 70 80 20 10 10 80 60 90 90 90 100 80 Foxtail, Giant 80 40 100 60 90 60 100 90 100 90 90 80 90 70 70 30 90 50 0 0 80 50 90 90 90 90 80 Morningglory 100 90 100 90 100 100 100 90 100 90 100 50 100 50 20 70 100 60 10 0 100 100 100 90 80 70 10 Pigweed 100 80 100 100 100 100 100 100 100 100 100 100 100 90 70 100 100 100 50 50 100 100 100 100 100 100 100 Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 70 70 100 100 100 100 100 100 100 Wheat 40 20 20 10 60 40 50 40 60 0 0 60 0 20 10 10 50 0 0 0 0 0 30 0 0 0 0 500 g ai/ha Compounds 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 Barnyardgrass 90 30 80 80 100 100 60 100 90 90 90 90 90 90 90 100 100 90 100 90 90 100 90 90 100 60 Corn 10 0 20 10 20 30 10 60 40 60 40 50 10 30 50 40 20 20 70 30 20 30 80 70 80 10 Crabgrass, Large 90 60 90 90 100 100 80 100 100 100 90 100 70 80 90 90 90 90 100 100 90 90 100 100 100 70 Foxtail, Giant 90 40 90 90 100 100 80 100 90 90 90 100 80 70 80 90 90 90 100 100 80 90 90 100 90 60 Morningglory 90 50 70 100 90 100 80 100 100 100 90 100 70 80 80 90 100 70 100 100 100 80 100 100 100 100 Pigweed 100 80 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Velvetleaf 100 — 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Wheat 0 0 0 30 20 30 0 0 0 40 0 0 0 0 0 20 40 0 0 20 0 0 0 40 50 0 500 g ai/ha Compounds 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 Barnyardgrass 70 90 90 90 90 90 90 90 90 90 50 90 90 90 100 80 60 90 90 90 90 80 90 70 90 80 Corn 10 50 40 20 30 10 10 70 50 60 0 60 10 10 40 20 20 10 60 20 50 20 20 20 60 50 Crabgrass, Large 90 90 90 90 100 100 90 90 90 90 60 90 90 100 100 90 80 90 90 90 90 90 80 70 90 90 Foxtail, Giant 60 90 90 90 90 90 80 90 80 80 40 80 60 70 90 90 60 60 90 80 90 70 70 50 80 90 Morningglory 90 100 60 100 100 90 100 100 100 100 60 90 100 90 100 100 100 90 100 100 100 90 100 100 100 100 Pigweed 100 100 100 100 100 100 100 100 100 100 60 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Wheat 0 0 10 0 10 50 0 20 0 30 0 0 30 0 10 0 0 0 50 20 50 10 0 0 50 0 500 g ai/ha Compounds 81 82 83 84 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 Barnyardgrass 100 70 90 10 90 90 90 90 90 90 100 90 90 90 90 90 90 90 90 90 90 90 60 40 50 50 Corn 70 20 30 20 80 50 50 60 10 20 10 20 30 10 10 20 80 60 20 0 10 20 20 0 10 10 Crabgrass, Large 90 90 90 10 90 90 90 90 100 90 100 90 100 90 90 100 100 100 100 90 90 100 40 0 70 70 Foxtail, Giant 90 80 90 0 90 90 90 90 90 80 80 90 90 80 90 90 80 90 90 90 80 90 20 0 20 60 Morningglory 100 100 100 90 100 90 100 100 100 100 100 100 100 100 100 100 100 100 100 100 70 100 100 100 80 100 Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 80 100 100 Wheat 30 0 0 0 40 50 60 0 20 40 50 0 0 0 0 20 20 20 0 30 0 10 0 0 0 0 500 g ai/ha Compounds 107 108 109 110 111 112 113 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 Barnyardgrass 90 90 90 90 90 90 90 90 90 100 90 90 90 90 100 80 90 90 90 90 90 100 100 100 90 90 Corn 50 40 30 10 30 20 60 50 20 10 50 30 70 50 40 30 70 20 20 60 20 60 50 50 30 40 Crabgrass, Large 90 90 100 90 90 90 100 90 90 80 100 90 90 100 100 90 90 90 90 90 90 90 90 100 90 70 Foxtail, Giant 90 90 90 50 90 80 100 80 80 90 80 90 90 90 90 80 80 70 90 80 80 90 90 90 90 70 Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 80 100 100 100 100 100 100 90 Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 90 Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Wheat 10 0 0 0 0 10 60 0 0 0 30 10 60 70 60 50 20 0 10 20 0 20 20 30 0 30 500 g ai/ha Compounds 133 134 135 136 138 139 140 141 142 143 144 145 146 147 148 149 150 151 152 153 154 155 156 157 158 159 Barnyardgrass 90 60 30 80 90 80 90 90 90 90 100 100 100 90 100 90 80 90 100 90 90 100 90 100 90 100 Corn 40 20 0 0 20 40 20 30 20 20 30 40 30 30 60 30 0 10 50 20 10 40 20 30 50 70 Crabgrass, Large 100 80 70 90 90 80 90 90 90 90 90 90 90 90 90 70 50 70 100 90 100 90 80 100 100 90 Foxtail, Giant 90 70 0 50 90 80 90 90 80 80 90 80 90 80 90 80 70 70 100 80 90 90 90 100 90 100 Morningglory 70 60 90 100 100 100 100 100 100 100 70 90 90 100 100 100 100 100 100 60 70 100 100 30 100 100 Pigweed 100 80 90 100 100 100 100 100 100 90 90 100 100 100 100 100 60 100 100 100 100 100 100 100 100 100 Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 90 100 100 100 100 100 100 100 100 100 Wheat 40 0 0 0 20 40 0 0 20 10 0 0 50 60 0 50 20 20 70 10 0 30 20 0 50 60 500 g ai/ha Compounds 160 161 162 163 164 165 166 167 168 169 170 171 172 173 174 175 176 177 178 179 180 181 182 183 184 185 Barnyardgrass 100 90 100 100 100 80 100 100 100 100 90 90 90 100 100 100 90 100 90 90 100 100 90 90 100 90 Corn 60 10 50 20 50 30 40 30 30 30 30 40 30 20 20 20 10 0 70 80 40 50 20 80 80 50 Crabgrass, Large 90 90 100 90 100 50 90 90 90 100 90 90 80 90 90 80 60 70 80 100 100 90 90 100 100 70 Foxtail, Giant 80 90 100 50 100 30 90 90 90 100 80 90 90 90 60 80 70 40 80 90 100 100 80 100 100 80 Morningglory 100 100 100 100 100 100 — 100 100 100 100 100 100 100 60 80 50 10 100 100 100 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— — 60 90 10 0 0 0 30 20 0 0 0 — 10 40 60 0 — 0 0 0 0 0 20 0 50 0 50 50 0 0 Pigweed 90 70 90 90 80 80 100 80 0 90 90 90 100 60 — 50 100 90 100 50 80 50 100 60 100 90 80 90 — — — — 90 80 Velvetleaf 80 70 100 80 60 70 80 60 30 70 70 70 70 70 50 90 80 70 90 20 70 20 70 50 100 50 70 0 70 — 100 80 70 70 Wheat 0 0 0 0 0 0 — 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 0 0 0 0 0 0 0 — 10 0 0 0 125 g ai/ha Compounds 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 107 108 109 110 111 112 113 114 115 116 117 Barnyardgrass 60 60 80 0 40 90 60 0 10 40 20 40 0 0 0 10 40 30 10 20 30 0 10 30 0 10 50 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 0 0 0 0 0 0 0 0 0 0 Crabgrass, Large 90 90 90 30 50 100 100 90 60 80 70 80 40 0 30 70 90 70 40 40 90 60 70 90 20 30 60 Foxtail, Giant 40 70 60 0 30 50 60 40 40 50 30 80 0 0 30 40 60 30 0 0 — 20 70 40 20 10 20 Morningglory 20 0 80 10 70 80 70 70 — 70 80 80 20 0 0 50 70 80 40 40 50 0 30 0 60 0 40 Pigweed 90 100 100 70 90 100 100 100 90 80 70 60 90 80 80 80 100 90 90 80 100 20 100 100 70 60 90 Velvetleaf 100 90 90 40 90 100 100 90 80 60 80 80 60 0 0 40 100 80 70 60 90 40 100 70 60 30 70 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 125 g ai/ha Compounds 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135 136 138 139 140 141 142 143 144 Barnyardgrass 30 70 70 20 30 50 20 10 70 40 10 30 20 50 10 10 0 0 0 20 40 60 60 10 40 0 Corn 0 20 20 0 0 0 0 0 0 0 0 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass, Large 60 100 100 90 90 100 60 80 90 90 80 70 40 80 50 50 0 0 20 40 90 70 80 30 50 10 Foxtail, Giant 10 90 90 80 30 50 10 40 60 50 60 40 20 60 20 40 0 0 0 30 20 40 40 0 10 0 Morningglory 10 60 30 0 40 70 60 0 70 10 80 — 10 — 0 0 — 20 30 0 0 30 0 0 10 0 Pigweed 90 100 100 80 100 90 100 90 100 100 80 100 90 100 10 40 0 40 80 50 70 80 70 90 70 0 Velvetleaf 70 90 80 80 100 70 70 60 80 70 80 80 80 80 50 50 70 40 70 20 60 80 70 20 70 20 Wheat 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 125 g ai/ha Compounds 145 146 147 148 149 150 151 152 153 154 155 156 157 158 159 160 161 162 163 164 165 166 167 168 169 170 Barnyardgrass 20 60 70 10 20 0 20 50 40 0 10 0 0 20 30 40 10 10 0 10 0 0 0 0 0 0 Corn 0 0 0 0 0 0 0 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass, Large 50 60 100 0 30 0 10 90 80 10 60 10 20 70 80 80 50 90 0 30 0 10 20 30 40 10 Foxtail, Giant 30 30 70 0 10 0 20 60 20 10 30 10 10 10 60 20 50 30 0 40 0 0 10 10 40 10 Morningglory 0 10 40 0 0 0 — 60 20 0 0 0 0 0 0 70 0 0 0 10 — 0 0 0 0 0 Pigweed 70 70 90 0 80 0 50 100 100 30 90 70 0 100 100 80 90 100 0 60 0 0 10 10 0 30 Velvetleaf 90 70 80 30 40 0 50 60 100 40 60 0 60 50 70 60 70 60 10 40 0 40 70 0 20 10 Wheat 0 0 0 0 0 0 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 125 g ai/ha Compounds 171 172 173 174 175 176 177 178 179 180 181 182 183 184 185 186 187 188 189 190 191 192 193 194 195 196 Barnyardgrass 20 10 0 0 0 10 0 0 0 30 20 70 20 20 0 0 20 0 20 10 10 10 80 0 0 0 Corn 0 0 0 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 40 0 0 0 0 Crabgrass, Large 70 10 40 20 30 0 0 10 20 80 90 100 90 30 0 30 30 30 30 60 50 10 90 20 0 0 Foxtail, Giant 30 10 20 0 0 10 0 10 10 30 30 50 60 30 0 20 30 10 30 60 40 0 90 — 0 0 Morningglory 0 0 0 0 0 0 0 0 0 0 0 70 20 10 — 20 80 70 — — 0 0 80 — 0 0 Pigweed 50 10 50 30 60 60 0 0 50 90 100 90 90 70 0 50 60 60 70 70 80 0 100 50 0 0 Velvetleaf 80 50 70 20 40 10 10 0 50 80 70 70 100 80 0 60 70 70 70 70 60 0 100 30 0 0 Wheat 20 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 125 g ai/ha Compounds 197 198 199 200 202 203 204 205 206 207 208 209 210 211 212 213 214 215 216 218 219 220 221 222 223 224 Barnyardgrass 0 0 20 0 20 30 30 0 0 10 10 0 10 10 10 0 10 0 0 20 40 10 0 0 0 0 Corn 0 0 20 0 20 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 Crabgrass, Large 0 10 60 0 50 20 40 20 10 60 80 20 10 10 0 0 30 0 0 10 50 20 0 20 30 70 Foxtail, Giant 0 70 60 0 50 30 20 10 0 30 40 10 20 20 10 10 30 10 0 0 10 0 0 30 30 20 Morningglory 0 0 70 0 0 0 0 0 0 0 0 0 0 0 0 — 0 0 0 0 20 0 0 0 10 — Pigweed 20 10 80 0 90 100 100 10 30 80 60 0 60 40 60 50 70 20 0 20 90 80 0 0 60 70 Velvetleaf 40 0 90 0 70 50 50 10 0 70 60 60 40 30 50 40 90 0 0 50 30 40 20 0 0 50 Wheat 0 0 0 0 0 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 125 g ai/ha Compounds 225 226 227 228 229 230 231 232 233 234 235 236 237 238 239 240 241 242 243 244 245 246 247 248 249 250 Barnyardgrass 20 30 50 40 0 10 0 0 30 0 90 50 20 70 20 40 10 0 70 30 40 10 0 0 0 0 Corn 0 0 0 0 0 0 0 0 0 0 20 0 0 0 0 0 0 0 30 20 0 0 0 0 0 0 Crabgrass, Large 60 90 90 100 80 30 40 10 40 60 100 80 40 90 70 50 20 0 100 90 80 100 0 10 40 30 Foxtail, Giant 40 70 40 50 50 40 0 0 20 10 70 40 40 50 20 40 10 0 90 70 80 90 0 10 20 30 Morningglory 30 60 50 70 40 0 10 0 50 — 80 70 10 40 — 0 0 0 70 30 20 20 0 0 30 10 Pigweed 90 100 80 100 90 — 50 0 70 50 90 80 30 100 70 20 20 0 100 100 80 100 0 0 80 60 Velvetleaf 80 80 90 100 100 60 50 0 60 30 100 80 80 90 80 60 20 0 90 50 70 90 0 20 60 50 Wheat 0 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 0 0 30 0 0 0 0 0 0 0 125 g ai/ha Compounds 251 252 253 254 255 256 Barnyardgrass 0 0 10 0 10 0 Corn 0 0 0 0 0 0 Crabgrass, Large 20 10 30 0 20 10 Foxtail, Giant 10 0 20 0 0 0 Morningglory 0 0 40 0 40 0 Pigweed 0 0 20 0 70 0 Velvetleaf 50 20 50 0 60 20 Wheat 0 0 0 0 0 0

Test B

Seeds of plant species selected from blackgrass (Alopecurus myosuroides), downy bromegrass (Bromus tectorum), green foxtail (Setaria viridis), Italian ryegrass (Lolium multiflorum), wheat (Triticum aestivum), wild oat (Avena fatua), deadnettle (henbit deadnettle, Lamium amplexicaule), galium (catchweed bedstraw, Galium aparine), bermudagrass (Cynodon dactylon), Surinam grass (Brachiaria decumbens), cocklebur (Xanthium strumarium), corn (Zea mays), large crabgrass (Digitaria sanguinalis), woolly cupgrass (Eriochloa villosa), giant foxtail (Setaria faberii), goosegrass (Eleusine indica), johnsongrass (Sorghum halepense), kochia (Kochia scoparia), lambsquarters (Chenopodium album), morningglory (Ipomoea coccinea), nightshade (eastern black nightshade, Solanum ptycanthum), yellow nutsedge (Cyperus esculentus), pigweed (Amaranthus retroflexus), ragweed (common ragweed, Ambrosia elatior), Russian thistle (Salsola kali), soybean (Glycine max), sunflower (common oilseed sunflower, Helianthus annuus) and velvetleaf (Abutilon theophrasti) were planted into a blend of loam soil and sand and treated preemergence with test compounds formulated in a non-phytotoxic solvent mixture which included a surfactant.

At the same time, plants selected from these crop and weed species and also winter barley (Hordeum vulgare), canarygrass (Phalaris minor), chickweed (Stellaria media) and windgrass (Apera spica-venti) were planted in pots containing Redi-Earth® planting medium (Scotts Company, 14111 Scottslawn Road, Marysville, Ohio 43041) comprising spaghnum peat moss, vermiculite, wetting agent and starter nutrients and treated with postemergence applications of some of the test chemicals formulated in the same manner. Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage) for postemergence treatments.

Plant species in the flooded paddy test consisted of rice (Oryza sativa), umbrella sedge (Cyperus difformis), ducksalad (Heteranthera limosa) and barnyardgrass (Echinochloa crus-galli) grown to the 2-leaf stage for testing. At the time of treatment, test pots were flooded with water to 3 cm above the soil surface, treated by application of test compounds directly to the paddy water, and then maintained at that water depth for the duration of the test.

Treated plants and controls were maintained in a greenhouse for 13 to 15 days, after which time all treated plants were visually evaluated and compared to controls. Plant response ratings, summarized in Table B, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.

TABLE B Flood 250 g ai/ha Compounds 1 2 3 4 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 Barnyardgrass 0 0 0 20 0 45 50 0 25 0 35 0 35 10 25 50 15 0 0 0 0 20 0 0 40 20 30 0 0 40 40 0 0 15 0 0 30 40 30 0 Ducksalad 0 78 70 85 0 90 75 80 80 55 95 40 60 75 45 90 90 75 75 60 45 75 0 85 85 85 85 50 75 95 95 65 0 40 60 65 90 90 75 50 Rice 0 8 0 0 0 50 0 0 25 0 25 0 0 10 15 25 0 15 0 0 15 0 0 0 0 0 0 0 0 30 50 0 — 35 20 0 15 25 0 20 Sedge, Umbrella 0 75 60 90 0 95 75 55 85 65 85 40 30 50 80 85 95 60 65 65 45 75 0 85 85 80 80 50 75 90 85 40 0 20 40 40 90 85 80 30 250 g ai/ha Compounds 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 Barnyardgrass 20 30 30 0 20 35 0 60 55 55 75 0 20 35 25 0 45 40 20 0 10 0 0 45 0 20 30 20 0 30 0 40 60 0 65 0 30 30 60 Ducksalad 80 90 90 20 95 85 70 85 95 70 75 40 50 50 60 0 40 60 0 30 40 60 0 20 0 40 20 0 0 0 0 0 50 0 40 20 40 30 40 Rice 40 40 20 10 25 65 15 20 60 60 85 0 25 20 25 0 15 15 0 0 10 0 0 20 0 30 0 20 0 20 0 0 45 0 15 20 20 15 15 Sedge, Umbrella 80 90 85 65 85 75 85 95 90 40 90 40 60 75 75 0 75 85 0 0 0 40 0 50 0 0 40 20 25 30 0 60 50 0 40 40 30 40 40 250 g ai/ha Compounds 82 83 84 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 107 108 109 110 111 112 Barnyardgrass 20 40 0 65 60 60 60 40 30 65 45 85 60 70 85 75 50 55 75 40 70 0 0 0 15 60 30 20 40 60 40 Ducksalad 20 50 20 65 65 20 80 100 90 100 85 80 30 20 75 70 0 80 85 30 85 0 0 0 0 40 70 100 75 75 95 Rice 20 30 0 20 40 70 50 15 0 15 40 45 35 30 15 40 40 60 — 20 35 0 0 0 20 45 10 25 30 30 15 Sedge, Umbrella 50 50 50 80 85 70 65 85 80 100 85 90 85 75 90 80 75 85 85 65 75 0 0 0 0 85 95 80 75 85 90 250 g ai/ha Compounds 113 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135 136 138 139 Barnyardgrass 15 40 65 75 75 70 50 65 70 40 70 30 60 75 75 40 60 85 50 30 0 0 0 25 25 35 Ducksalad 70 75 85 85 100 100 70 85 80 0 95 0 70 85 80 100 100 100 85 100 100 0 40 75 80 90 Rice 0 20 20 0 15 15 35 40 55 15 40 20 0 15 35 35 30 25 55 0 0 0 0 20 15 30 Sedge, Umbrella 70 40 90 90 95 85 75 75 70 45 85 40 90 85 80 75 60 100 85 100 100 0 0 50 80 85 250 g ai/ha Compounds 140 141 142 143 144 145 146 147 148 151 152 153 154 155 156 158 161 162 164 178 179 183 184 185 186 187 Barnyardgrass 45 50 10 20 20 25 30 75 50 55 75 45 40 45 60 60 30 55 0 80 30 35 25 0 30 80 Ducksalad 85 85 80 90 100 80 100 100 100 100 100 100 100 95 100 100 80 100 85 100 100 95 100 75 100 100 Rice 40 35 0 0 25 0 35 15 50 50 60 65 75 45 35 85 50 90 35 70 65 0 15 0 65 70 Sedge, Umbrella 85 85 80 65 100 80 90 80 95 100 100 95 100 100 100 100 60 100 90 95 95 90 95 60 90 100 250 g ai/ha Compounds 188 189 190 191 192 193 194 195 196 197 198 199 200 203 204 206 207 208 209 210 211 212 213 214 215 216 Barnyardgrass 0 70 30 25 0 50 15 20 30 30 35 25 38 20 60 0 20 25 20 40 35 50 30 20 40 0 Ducksalad 85 100 100 100 75 100 80 85 95 85 95 90 85 95 100 90 50 75 85 90 85 95 100 95 85 95 Rice 15 60 15 0 20 65 0 15 65 45 50 0 23 0 60 20 15 0 20 25 15 10 20 15 15 0 Sedge, Umbrella 85 100 95 85 60 90 65 65 80 85 80 85 70 85 95 85 70 70 80 80 80 95 90 85 90 100 250 g ai/ha Compounds 217 218 219 220 221 222 223 224 226 227 228 229 230 231 232 233 234 235 236 237 238 239 243 244 245 246 Barnyardgrass 0 40 60 40 20 0 0 30 95 60 80 30 40 40 50 65 0 75 20 30 40 15 85 75 65 60 Ducksalad 40 95 90 100 70 65 0 75 40 80 80 40 0 0 85 100 70 100 70 100 100 80 100 100 100 100 Rice 20 15 75 70 15 0 0 60 65 55 60 20 45 0 0 50 0 55 0 45 0 0 75 85 90 65 Sedge, Umbrella 40 85 85 85 75 40 0 75 60 85 85 70 75 75 80 85 40 80 40 100 80 75 100 100 100 100 250 g ai/ha 125 g ai/ha Compounds Compounds 248 249 250 251 252 253 254 255 256 1 2 3 4 7 8 9 10 11 12 13 14 16 17 18 19 20 21 22 23 33 34 35 36 37 Barnyardgrass 40 0 10 20 0 20 15 0 0 0 0 0 0 0 20 0 0 0 0 0 0 0 25 20 0 0 0 0 0 30 0 0 0 0 Ducksalad 90 90 75 80 0 90 100 80 85 0 58 70 75 0 85 60 75 65 35 0 30 75 30 65 85 65 70 30 45 80 30 0 0 50 Rice 0 15 0 10 0 20 0 0 0 0 0 0 0 0 15 0 0 20 0 0 0 0 0 25 0 0 0 0 0 20 0 0 20 0 Sedge, Umbrella 85 90 70 75 0 85 80 60 75 0 45 60 80 0 85 70 55 40 50 60 0 40 70 50 85 50 60 40 40 50 0 0 0 30 125 g ai/ha Compounds 38 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 76 79 80 81 82 83 84 85 86 87 88 89 90 Barnyardgrass 0 0 35 40 40 55 0 20 20 20 0 20 30 0 0 0 0 0 0 0 0 20 0 0 0 0 20 25 40 15 15 0 55 50 55 40 30 15 Ducksalad 60 40 85 85 40 75 30 0 40 40 0 0 40 0 0 40 50 0 0 0 30 0 0 0 0 0 15 30 15 0 40 0 60 55 20 75 100 80 Rice 0 10 15 25 50 60 0 15 15 15 0 15 0 0 0 0 0 0 0 0 20 0 0 0 20 0 15 0 15 15 0 0 15 20 60 40 0 0 Sedge, Umbrella 30 0 85 85 30 90 0 40 60 50 0 50 75 0 0 0 0 0 30 0 0 0 20 0 0 0 0 30 30 40 40 30 80 70 50 40 85 75 125 g ai/ha Compounds 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 108 109 110 111 123 124 125 126 127 128 129 130 132 Barnyardgrass 60 20 75 40 65 80 60 30 20 60 40 60 0 0 0 0 15 20 20 50 55 0 40 60 65 15 10 0 0 Ducksalad 90 70 80 25 0 50 30 0 75 85 30 80 0 0 0 0 60 65 75 75 90 0 60 85 60 95 90 80 80 Rice 15 25 20 20 30 15 0 0 0 35 0 20 0 0 0 20 0 20 30 0 30 20 0 0 25 10 0 0 0 Sedge, Umbrella 100 70 80 85 50 85 70 75 65 80 30 65 0 0 0 0 60 75 50 80 75 20 90 80 60 60 60 75 60 125 g ai/ha Compounds 133 142 143 144 145 146 147 148 151 152 153 154 155 156 157 158 161 162 163 164 166 167 168 170 171 172 Barnyardgrass 0 0 0 0 0 0 45 15 30 50 35 0 20 40 0 20 0 40 0 0 20 20 0 30 20 20 Ducksalad 100 80 80 75 80 80 80 90 100 100 100 70 85 80 70 100 0 100 60 0 60 70 30 45 70 60 Rice 0 0 0 20 0 0 10 20 15 30 55 60 25 20 0 40 45 90 20 20 0 0 0 20 0 0 Sedge, Umbrella 95 65 0 95 60 80 40 85 100 85 80 95 85 100 75 100 0 100 70 0 70 60 20 35 80 75 125 g ai/ha Compounds 173 174 175 176 177 178 179 180 181 182 183 184 185 186 190 191 192 193 194 195 196 197 198 199 200 203 Barnyardgrass 15 0 20 0 15 60 20 15 70 0 0 20 0 30 20 0 0 45 10 0 20 20 30 15 23 0 Ducksalad 75 95 95 75 70 100 95 75 90 85 80 100 75 90 40 75 75 85 50 70 95 80 85 85 85 95 Rice 15 0 0 20 20 70 25 30 65 0 0 15 0 45 15 0 0 30 0 0 40 30 20 0 10 0 Sedge, Umbrella 85 95 85 85 75 95 85 65 85 75 65 80 65 80 30 80 50 70 0 50 75 75 80 75 43 75 125 g ai/ha Compounds 204 207 208 209 210 211 212 213 215 216 218 219 220 221 223 224 226 227 228 229 230 235 236 237 238 239 Barnyardgrass 25 0 15 0 20 25 0 0 30 0 30 20 30 0 0 0 95 50 75 0 20 50 0 0 30 0 Ducksalad 90 0 40 85 90 85 90 90 85 90 85 65 85 70 0 0 30 75 75 0 0 100 60 90 80 70 Rice 0 15 0 10 20 0 0 0 0 0 10 70 50 0 0 0 60 45 35 0 30 45 0 0 0 0 Sedge, Umbrella 90 60 40 70 75 70 90 85 75 80 85 60 20 75 0 0 50 85 75 50 40 80 0 55 65 40 125 g ai/ha 62 g ai/ha Compounds Compounds 243 244 245 246 248 249 250 251 253 254 255 256 1 2 3 4 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 Barnyardgrass 75 40 40 20 0 0 10 0 0 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 0 20 20 0 0 0 0 0 Ducksalad 100 100 100 100 80 80 70 50 85 85 60 80 0 40 0 40 0 85 30 20 0 25 0 20 0 40 30 50 75 60 70 20 35 Rice 95 60 50 65 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 0 15 0 0 0 0 0 Sedge, Umbrella 100 100 100 100 75 85 65 65 75 75 50 75 0 0 50 65 0 65 30 40 0 40 0 0 0 0 70 30 70 40 50 30 30 62 g ai/ha Compounds 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 Barnyardgrass 0 0 0 0 10 0 0 0 10 20 0 0 0 0 0 0 0 0 0 20 0 0 0 0 0 0 0 20 0 40 0 20 15 0 0 0 0 0 Ducksalad 20 0 75 75 70 70 20 60 75 75 0 0 0 30 20 80 0 70 30 70 80 20 20 65 0 0 75 30 0 65 0 0 20 0 0 0 0 0 Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 15 10 15 0 0 10 15 0 20 0 10 0 0 0 15 0 0 Sedge, Umbrella 0 0 75 75 70 70 20 60 75 30 0 0 0 20 0 90 70 70 30 30 80 70 45 70 40 0 75 40 30 85 0 30 40 0 0 40 30 0 62 g ai/ha Compounds 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100 Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 20 0 30 0 0 20 0 0 0 0 25 40 45 20 20 0 20 0 60 0 35 65 40 30 20 45 Ducksalad 0 20 30 0 0 0 0 0 0 0 0 0 0 30 0 30 0 0 20 0 0 30 0 50 55 30 40 90 65 90 30 55 20 0 0 30 0 40 75 Rice 0 0 0 0 0 0 15 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 0 0 0 15 0 15 0 20 15 0 0 0 30 Sedge, Umbrella 0 0 0 0 0 0 0 0 0 0 0 0 30 0 0 40 30 0 20 0 0 30 0 75 30 20 30 85 60 95 65 75 70 20 75 40 65 50 75 62 g ai/ha Compounds 101 102 103 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118 119 120 121 122 123 124 125 126 Barnyardgrass 40 60 0 0 0 0 40 0 0 0 40 35 10 20 50 65 65 50 30 20 30 20 40 0 25 45 Ducksalad 30 40 0 0 0 0 0 50 60 40 30 85 25 65 85 80 — 100 30 30 45 0 80 0 40 80 Rice 0 15 0 0 0 0 20 0 0 0 0 0 0 0 20 0 0 0 20 0 0 0 20 15 0 0 Sedge, Umbrella 20 40 0 0 0 0 60 40 60 35 75 85 40 30 70 75 95 70 25 40 30 20 70 0 35 70 62 g ai/ha Compounds 127 128 129 130 131 132 133 134 135 136 138 139 140 141 142 143 144 145 146 147 148 151 152 153 154 155 Barnyardgrass 40 10 0 0 20 0 0 0 0 20 0 10 20 20 0 0 0 0 0 10 0 15 25 0 0 0 Ducksalad 30 95 90 80 40 50 60 0 30 55 70 75 50 75 0 80 60 80 60 60 90 80 90 65 50 60 Rice 15 0 0 0 25 0 0 0 0 15 0 10 0 0 0 0 20 0 0 0 10 0 20 35 0 0 Sedge, Umbrella 20 30 0 60 20 0 60 0 0 45 70 70 75 80 0 0 65 0 50 40 80 85 0 0 95 60 62 g ai/ha Compounds 156 158 161 162 164 178 179 183 184 185 186 187 188 189 190 191 192 193 194 195 196 197 198 199 200 203 Barnyardgrass 20 20 0 25 0 20 10 0 0 0 20 45 0 30 0 0 0 20 0 0 0 0 0 0 0 0 Ducksalad 65 75 0 100 0 75 90 65 100 70 90 95 70 100 20 85 60 50 50 50 60 65 50 85 83 75 Rice 30 30 50 25 0 20 0 0 15 0 20 15 0 20 15 0 0 15 0 0 0 0 20 0 0 0 Sedge, Umbrella 95 85 0 100 0 85 80 50 80 75 80 95 80 95 0 75 40 30 0 0 30 70 20 70 33 65 62 g ai/ha Compounds 204 206 207 208 209 210 211 212 213 214 215 216 217 218 219 220 221 222 223 224 226 227 228 229 230 231 Barnyardgrass 15 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 60 40 40 0 0 40 Ducksalad 70 70 0 30 50 85 — 85 85 0 75 90 0 80 20 40 65 50 0 0 0 — 50 0 0 0 Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 15 0 0 0 0 40 30 20 0 20 0 Sedge, Umbrella 75 60 40 40 50 75 0 85 80 0 0 65 40 80 40 0 60 30 0 0 40 85 75 0 30 0 62 g ai/ha 31 g ai/ha Compounds Compounds 232 233 234 235 236 237 238 239 243 244 245 246 248 249 250 251 252 253 254 255 256 1 2 3 4 7 8 9 Barnyardgrass 30 20 0 20 0 0 0 0 30 20 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 85 100 20 95 0 65 40 0 85 80 100 100 80 65 30 0 0 75 85 50 40 0 15 0 20 0 30 0 Rice 0 25 0 0 0 0 0 0 60 0 50 30 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Sedge, Umbrella 80 70 0 70 0 45 0 0 90 0 100 85 65 60 65 50 0 65 50 20 40 0 0 40 50 0 30 0 31 g ai/ha Compounds 10 11 12 13 14 16 17 18 19 20 21 22 23 33 34 35 36 37 38 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 Barnyardgrass 0 0 0 0 0 0 0 10 0 0 0 0 0 0 0 0 0 0 0 0 0 15 0 20 0 0 10 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 0 0 0 0 0 0 0 20 0 60 60 0 20 60 0 0 0 0 0 0 70 0 0 40 0 0 0 0 0 0 0 0 0 0 30 0 0 0 0 Rice 0 0 0 0 0 0 0 10 0 0 0 0 0 0 0 0 0 0 0 0 0 10 0 15 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Sedge, Umbrella 0 0 20 0 0 0 0 0 0 0 40 0 20 20 0 0 0 0 0 0 75 30 20 40 0 0 30 0 0 30 0 0 0 0 0 0 0 0 0 31 g ai/ha Compounds 69 70 71 72 76 79 80 81 82 83 84 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 108 109 Barnyardgrass 0 0 0 0 0 0 15 0 0 0 0 25 30 20 0 20 0 15 0 30 0 20 60 30 0 0 20 20 15 0 0 0 0 0 0 Ducksalad 0 0 0 0 0 0 0 0 0 20 0 40 0 20 30 45 50 65 20 40 0 0 0 30 0 30 35 20 30 0 0 0 0 40 50 Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 10 0 0 0 0 0 0 Sedge, Umbrella 0 0 0 0 0 0 0 0 0 0 0 50 20 0 0 30 50 75 65 70 20 0 50 30 40 50 40 0 30 0 0 0 0 0 50 31 g ai/ha Compounds 110 111 123 124 125 126 127 128 129 130 132 133 142 143 144 145 146 147 148 151 152 153 154 155 156 157 Barnyardgrass 0 0 30 0 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 0 15 0 0 0 0 0 Ducksalad 0 30 30 0 20 75 0 90 0 60 0 60 0 80 50 80 0 60 90 80 0 0 0 0 0 50 Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 15 0 0 0 20 20 20 35 0 0 30 0 Sedge, Umbrella 30 0 40 0 25 50 0 0 0 40 0 0 0 0 50 0 0 0 80 85 0 0 0 60 0 40 31 g ai/ha Compounds 158 161 162 163 164 166 167 168 170 171 172 173 174 175 176 177 178 179 180 181 182 183 184 185 186 190 Barnyardgrass 20 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 20 0 0 0 0 0 0 0 0 0 Ducksalad 50 0 98 30 0 0 0 0 0 40 20 30 80 75 40 30 75 90 60 85 60 30 95 75 90 20 Rice 20 25 0 10 0 0 0 0 15 0 0 0 0 0 15 15 0 0 15 0 0 0 15 0 10 15 Sedge, Umbrella 70 0 95 70 0 50 20 0 0 70 0 0 85 75 70 60 55 40 20 75 50 0 65 65 70 0 31 g ai/ha Compounds 191 192 193 194 195 196 197 198 199 200 203 204 207 208 209 210 211 212 213 215 216 218 219 220 221 223 Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 65 60 40 40 0 40 65 40 85 38 40 50 0 0 0 75 50 85 75 70 50 75 0 30 20 0 Rice 0 0 0 0 0 0 0 15 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Sedge, Umbrella 60 0 0 0 0 20 65 20 60 30 0 70 0 0 0 50 0 80 65 0 0 75 20 0 0 0 31 g ai/ha Compounds 224 226 227 228 229 230 235 236 237 238 239 243 244 245 246 248 249 250 251 253 254 255 256 Barnyardgrass 0 50 20 15 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 0 0 — 40 0 0 95 0 0 0 0 0 35 100 85 75 0 30 0 60 45 0 30 Rice 0 20 20 0 0 0 0 0 0 0 0 45 0 50 0 0 0 0 0 0 0 0 0 Sedge, Umbrella 0 30 80 65 0 0 0 0 0 0 0 0 0 60 0 50 0 0 0 60 30 0 30 Postemergence 250 g ai/ha Compounds 1 3 4 7 8 9 10 11 12 14 24 26 27 29 33 34 36 37 38 39 40 42 44 45 46 47 Barley 0 0 10 0 20 35 5 10 0 40 70 0 20 0 0 30 — 0 35 10 10 5 15 5 0 35 Bermudagrass 65 80 100 70 100 98 95 100 100 80 100 75 100 100 98 98 100 100 100 100 100 98 98 100 90 — Blackgrass 5 5 50 5 20 70 50 40 20 5 50 40 50 50 30 40 15 30 40 20 15 20 30 25 10 30 Bromegrass, Downy 10 45 55 5 10 50 20 45 20 70 75 40 30 45 20 50 65 45 85 0 85 25 85 50 25 55 Canarygrass 0 5 80 0 85 60 40 90 40 50 60 60 50 40 5 50 50 30 45 20 35 0 40 30 0 40 Chickweed 90 100 100 100 100 98 98 100 100 80 100 85 80 85 100 100 100 100 100 100 100 95 100 100 98 100 Cocklebur 85 100 100 70 100 45 98 100 100 98 100 100 98 98 95 95 — — — 98 — 95 98 95 90 100 Corn 0 15 85 10 80 80 65 85 75 70 85 50 70 60 15 50 85 75 90 65 90 45 85 80 75 — Crabgrass, Large 65 90 100 60 100 95 80 100 90 85 100 80 60 80 98 98 98 90 100 90 100 90 98 85 75 100 Cupgrass, Woolly 20 55 100 65 100 85 75 95 80 80 95 85 80 85 90 95 98 100 100 90 98 55 95 80 45 100 Deadnettle — — — — — — — — — — — — — — — — — — — — — — — — — — Foxtail, Giant 50 65 100 60 100 100 95 100 98 95 95 95 90 95 95 95 98 100 100 95 100 85 98 98 85 98 Foxtail, Green 40 50 60 40 95 95 70 98 70 85 95 95 90 90 90 95 90 95 95 90 95 85 90 95 85 95 Galium — — — — — — — — — — — — — — — — — — — — — — — — — — Goosegrass 80 95 98 35 100 100 98 98 100 85 98 95 98 95 85 95 95 95 95 75 98 95 95 90 80 98 Johnsongrass 20 15 98 0 100 95 75 98 75 80 80 70 80 45 40 100 100 85 100 98 100 65 95 100 75 — Kochia 45 95 100 50 100 85 20 98 65 — 100 — 100 — 98 100 65 65 100 95 75 100 95 98 30 100 Lambsquarters 90 100 100 75 100 95 95 98 98 85 100 98 98 98 100 100 100 100 100 100 100 100 98 100 95 100 Morningglory 65 70 95 20 100 75 55 80 95 95 90 75 90 98 85 95 75 95 100 95 85 98 80 90 80 95 Nutsedge, Yellow 45 80 80 0 85 70 75 60 80 50 70 35 55 70 80 65 60 65 55 45 — 70 55 60 75 70 Oat, Wild 10 50 50 10 35 55 40 70 20 50 80 60 65 80 55 70 85 80 85 40 90 25 85 70 30 60 Pigweed 90 100 100 98 100 100 100 98 100 98 80 98 100 85 100 98 98 100 100 100 100 100 100 100 80 100 Ragweed 75 100 100 85 100 100 98 100 100 98 98 100 100 100 98 98 95 98 95 98 98 85 98 98 80 95 Ryegrass, Italian 0 5 20 20 50 45 20 40 5 50 50 45 10 45 45 40 15 30 65 20 10 15 35 35 10 50 Soybean 80 90 100 85 100 98 98 100 100 90 100 98 100 98 100 100 100 100 100 100 100 95 95 98 90 98 Surinam Grass 20 65 90 25 80 85 80 85 85 55 80 60 80 85 90 85 95 95 95 70 100 65 95 95 90 100 Velvetleaf 90 100 100 98 100 98 85 100 100 100 98 98 90 98 100 100 100 100 100 95 100 98 100 95 90 100 Wheat 5 30 70 15 35 30 5 45 0 20 50 30 30 40 5 55 5 5 60 20 35 10 30 30 0 15 Windgrass 5 5 75 5 40 80 40 98 50 50 80 60 60 50 60 80 85 70 90 — 90 — — — 50 — 250 g ai/ha Compounds 48 49 50 51 52 53 55 56 58 59 61 62 63 64 66 67 68 70 71 72 73 74 75 77 79 80 Barley 10 0 5 50 25 70 0 — 10 10 0 30 0 35 0 30 30 90 5 0 10 0 0 0 55 75 Bermudagrass 100 98 100 98 100 98 90 100 100 100 90 90 95 98 95 85 98 98 98 85 90 98 98 95 85 55 Blackgrass 30 30 15 55 30 50 10 20 40 60 5 50 50 15 15 10 20 50 5 0 30 45 20 5 45 10 Bromegrass, Downy 70 5 20 60 70 60 0 60 50 45 5 50 40 85 25 5 40 70 30 20 60 35 50 5 65 80 Canarygrass 45 0 5 98 85 90 0 40 85 70 0 5 0 60 0 5 35 98 20 0 40 0 0 0 50 70 Chickweed 100 90 98 95 98 100 90 98 90 100 98 80 95 100 98 100 100 100 98 90 100 100 100 98 98 100 Cocklebur 98 85 90 90 85 90 75 95 90 100 85 75 95 95 45 90 90 40 95 95 80 95 95 85 98 65 Corn 85 15 25 85 80 85 10 70 80 75 15 80 45 90 75 75 80 75 15 10 85 60 55 75 75 65 Crabgrass, Large 95 85 98 90 98 100 85 95 90 100 75 85 90 98 70 95 98 100 95 90 95 95 100 85 95 95 Cupgrass, Woolly 95 55 85 90 95 98 20 85 95 95 60 65 65 98 75 75 75 90 100 50 65 75 80 40 75 75 Deadnettle — — — — — — — — — — — — — — — — — — — — — — — — — — Foxtail, Giant 98 75 95 85 90 95 75 95 98 95 75 80 80 100 95 90 90 98 95 80 90 85 95 80 95 95 Foxtail, Green 95 90 95 100 100 100 80 100 100 70 80 85 90 100 98 95 95 98 98 90 95 85 90 80 98 98 Galium — — — — — — — — — — — — — — — — — — — — — — — — — — Goosegrass 98 70 90 85 85 85 75 90 90 95 80 75 75 90 95 80 95 95 90 70 80 85 98 85 80 85 Johnsongrass 95 10 70 98 95 100 20 100 100 100 10 10 15 100 65 10 100 98 100 45 75 85 75 10 75 45 Kochia 100 90 100 35 65 80 85 100 25 75 85 80 65 80 98 85 98 98 65 90 90 98 100 95 80 60 Lambsquarters 100 98 100 98 95 98 98 100 100 100 98 100 98 100 100 100 100 100 98 100 100 98 100 98 100 100 Morningglory 80 85 80 100 85 98 85 100 90 80 80 75 75 90 100 100 100 100 80 90 95 100 95 90 100 100 Nutsedge, Yellow 70 70 75 80 65 75 65 75 75 75 65 55 60 25 70 70 80 60 25 75 70 70 75 80 80 75 Oat, Wild 85 40 30 90 95 85 5 45 85 80 5 40 20 98 10 10 70 95 5 40 95 80 60 5 75 50 Pigweed 100 98 100 100 98 100 95 100 100 100 98 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Ragweed 98 90 98 95 85 98 98 75 98 95 90 80 80 90 60 90 95 80 95 95 85 90 95 85 98 75 Ryegrass, Italian 30 0 0 30 60 45 0 50 70 80 0 50 10 30 10 5 50 70 5 30 70 35 60 10 55 5 Soybean 98 85 95 95 98 95 75 98 95 95 50 95 85 98 98 98 98 98 98 95 95 95 98 70 98 95 Surinam Grass 98 70 85 90 98 98 60 100 98 90 75 70 75 98 98 25 90 100 85 100 85 75 85 80 90 65 Velvetleaf 100 98 100 95 100 98 100 98 95 98 98 100 98 100 100 100 100 100 95 100 100 100 100 100 100 100 Wheat 30 30 15 30 35 50 10 0 0 60 10 30 10 55 0 25 10 35 5 10 50 50 25 10 40 35 Windgrass — 30 80 85 100 95 5 85 70 70 20 50 60 100 80 5 85 100 60 65 98 95 90 25 90 80 250 g ai/ha Compounds 81 82 83 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100 102 107 108 109 111 113 117 Barley 5 5 5 20 65 5 80 20 20 40 0 5 5 0 5 5 15 30 50 60 30 0 5 30 20 0 Bermudagrass 95 95 90 90 95 100 85 95 85 95 85 85 98 90 98 98 98 98 85 100 98 100 95 100 95 100 Blackgrass 30 15 0 50 55 40 10 30 30 50 5 30 20 5 40 50 50 15 40 45 20 30 50 40 5 40 Bromegrass, Downy 50 30 60 30 50 80 60 5 10 30 20 0 0 0 10 10 40 25 35 30 30 5 5 10 90 45 Canarygrass 20 35 25 60 85 35 90 60 30 75 0 10 35 0 45 30 50 70 10 50 80 5 45 15 90 5 Chickweed 100 100 100 98 98 100 95 98 90 100 100 98 100 100 100 100 100 98 100 100 100 100 100 100 100 100 Cocklebur 90 100 90 98 98 100 95 70 100 95 98 98 90 100 100 100 100 100 98 100 100 100 100 100 98 100 Corn 65 15 25 85 85 75 80 98 75 60 60 60 80 35 80 75 70 80 45 70 85 65 60 60 85 25 Crabgrass, Large 98 90 98 95 98 98 98 98 80 100 100 90 90 80 90 95 95 95 80 90 95 85 85 85 95 95 Cupgrass, Woolly 90 75 95 90 95 90 95 75 55 98 70 70 70 65 85 75 95 85 75 85 80 75 75 75 95 98 Deadnettle — — — — — — — — — — — — — — — — — — — — — — — — — — Foxtail, Giant 98 95 98 98 98 95 95 98 85 98 98 85 98 85 85 90 85 95 85 95 95 80 90 70 95 95 Foxtail, Green 95 90 98 98 100 95 100 80 90 98 98 90 80 90 85 95 95 98 85 95 98 80 98 70 95 95 Galium — — — — — — — — — — — — — — — — — — — — — — — — — — Goosegrass 80 85 95 85 95 98 70 80 75 85 90 75 85 90 85 98 90 80 75 90 85 85 85 85 90 85 Johnsongrass 100 95 100 98 100 45 100 100 65 100 100 70 45 45 80 85 98 95 25 75 90 60 75 40 95 25 Kochia 100 75 95 90 98 100 85 100 98 95 100 98 90 100 100 100 98 100 100 100 100 100 98 100 100 85 Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 98 100 100 100 100 100 100 98 100 100 100 100 100 98 100 Morningglory 100 100 100 100 100 65 95 100 100 98 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Nutsedge, Yellow 80 55 85 85 85 75 75 75 75 75 75 70 65 85 85 80 75 75 40 80 85 85 80 85 75 35 Oat, Wild 55 10 10 60 80 90 80 50 20 50 10 5 30 0 30 10 50 80 30 80 40 0 40 10 85 35 Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 98 98 100 100 100 100 100 100 Ragweed 100 95 98 98 98 98 98 100 95 98 75 98 80 95 95 100 90 95 80 95 98 98 98 98 98 98 Ryegrass, Italian 55 10 5 45 60 60 80 30 0 20 30 0 10 0 10 5 15 20 50 10 5 0 40 5 85 50 Soybean 98 98 95 95 98 100 98 98 100 98 98 98 95 98 98 100 100 100 100 100 100 85 100 98 98 95 Surinam Grass 100 80 90 85 100 85 98 95 75 98 75 70 80 70 85 85 90 80 75 85 85 80 80 80 90 85 Velvetleaf 100 95 100 98 100 100 98 100 100 100 100 98 80 100 100 100 98 100 85 100 100 100 100 100 98 100 Wheat 25 5 0 35 45 50 5 10 35 50 0 5 5 0 15 5 20 5 35 30 15 5 15 30 50 25 Windgrass 70 50 30 95 95 95 70 50 50 65 90 55 50 0 45 85 70 60 60 70 85 40 80 70 80 65 250 g ai/ha Compounds 118 119 120 121 123 126 127 128 129 130 140 141 146 147 152 155 156 157 160 162 164 173 181 184 186 187 Barley 0 5 5 10 50 40 60 5 0 0 0 5 30 0 90 85 85 30 50 85 35 50 55 60 5 40 Bermudagrass 98 98 98 100 98 95 98 100 98 95 90 90 100 98 98 100 98 100 95 100 100 100 100 100 98 100 Blackgrass 40 50 60 60 80 45 40 15 5 5 5 25 50 55 70 65 50 40 25 65 35 50 15 50 20 5 Bromegrass, Downy 35 85 80 90 45 40 40 50 35 40 20 45 35 10 85 50 40 65 55 50 95 70 85 60 50 40 Canarygrass 15 30 55 30 85 90 60 30 0 25 5 5 10 5 85 65 60 90 35 90 98 80 90 95 40 60 Chickweed 100 100 100 100 100 98 98 100 100 100 75 95 98 98 95 100 100 100 100 100 100 100 100 100 100 100 Cocklebur 98 95 80 100 100 98 100 100 100 100 95 100 — 100 100 100 98 100 100 100 100 100 100 100 100 100 Corn 25 70 75 85 80 80 75 60 60 80 45 45 35 40 80 65 60 100 60 85 70 85 95 98 65 80 Crabgrass, Large 95 95 98 98 90 90 95 100 85 100 90 85 98 90 95 90 80 100 95 98 100 100 100 100 95 100 Cupgrass, Woolly 95 100 100 100 90 90 85 95 85 90 65 70 75 80 100 75 65 98 95 100 100 100 100 100 85 95 Deadnettle — — — — — — — — — — — — — — — — — — — — — — — 100 100 100 Foxtail, Giant 95 95 98 98 85 90 90 98 98 98 90 85 98 90 98 95 90 100 85 98 100 100 100 100 95 100 Foxtail, Green 95 100 100 100 90 95 95 98 95 98 95 90 90 90 100 80 85 95 98 100 100 90 98 98 95 98 Galium — — — — — — — — — — — — — — — — — — — — — — — 60 70 85 Goosegrass 90 95 98 98 85 85 85 98 95 95 85 80 95 95 98 98 80 100 90 98 98 100 100 100 100 100 Johnsongrass 35 80 80 85 90 90 95 85 85 80 45 65 95 60 100 70 65 100 75 100 98 — 100 100 100 100 Kochia 98 100 98 100 100 85 100 98 98 100 35 90 90 100 100 100 25 45 100 80 100 100 100 10 100 80 Lambsquarters 100 100 100 100 98 98 95 100 98 100 80 100 100 100 100 100 100 100 98 100 100 100 100 100 100 100 Morningglory 80 95 90 45 100 100 98 90 90 100 65 65 95 100 95 100 100 100 100 100 100 95 100 100 100 100 Nutsedge, Yellow 65 75 75 50 80 80 80 60 85 40 75 60 40 75 80 75 75 45 80 80 75 75 85 75 80 75 Oat, Wild 40 95 95 98 60 50 60 80 30 60 40 40 70 45 85 70 50 70 60 55 90 85 100 98 45 45 Pigweed 100 100 100 100 100 98 100 100 98 100 98 98 100 100 100 100 100 98 100 100 100 100 100 100 100 100 Ragweed 98 98 80 95 98 90 98 98 95 98 75 95 98 98 98 95 90 100 98 100 100 98 100 — 100 100 Ryegrass, Italian 60 85 80 75 50 50 30 30 0 5 5 5 15 40 80 60 40 35 35 90 40 30 65 60 30 30 Soybean 100 80 98 100 90 98 98 98 98 100 80 90 100 85 100 100 98 100 98 100 100 100 100 100 100 100 Surinam Grass 90 98 100 100 85 98 90 85 85 90 65 75 75 75 95 75 70 100 75 85 98 — 100 100 — — Velvetleaf 100 100 100 100 100 98 100 100 100 100 85 98 100 100 100 100 100 100 100 100 95 100 100 100 100 100 Wheat 10 60 80 80 50 50 40 5 0 10 15 10 45 10 90 70 45 30 45 40 50 50 70 60 5 5 Windgrass 80 100 90 100 90 60 70 85 85 85 30 50 60 70 98 85 60 80 80 80 85 75 65 100 65 80 250 g ai/ha 125 g ai/ha Compounds Compounds 189 190 191 193 197 217 218 219 220 226 227 228 229 233 235 236 237 238 239 240 243 244 245 255 1 2 Barley 40 70 70 50 40 10 35 30 15 60 30 40 25 10 — 0 40 40 5 15 95 98 95 50 0 30 Bermudagrass 70 100 100 100 100 100 100 100 100 98 90 95 90 100 100 — 100 100 100 100 100 100 100 100 60 90 Blackgrass 5 40 60 60 45 30 5 90 40 60 20 55 30 50 — 40 80 70 50 65 98 85 80 60 5 45 Bromegrass, Downy 10 35 75 85 30 65 30 80 30 30 25 10 30 60 85 25 95 85 10 50 100 80 95 85 0 80 Canarygrass 10 55 85 25 60 20 5 55 30 60 10 10 60 20 30 10 50 30 0 40 100 100 100 60 0 80 Chickweed 100 100 100 100 100 100 100 100 100 95 90 100 98 100 100 100 100 100 100 100 100 100 100 100 65 95 Cocklebur 100 100 100 100 100 100 — — — 100 95 100 100 100 — 100 — — 100 — — — — — 70 95 Corn 45 65 85 60 65 35 80 80 75 98 85 90 85 85 100 — 100 95 75 100 100 100 100 85 0 35 Crabgrass, Large 100 90 100 100 100 98 90 98 90 98 90 98 90 100 100 100 100 98 98 100 100 100 100 95 55 90 Cupgrass, Woolly 80 85 98 98 98 55 80 98 65 95 95 98 90 100 100 — 100 100 95 100 100 100 100 98 0 85 Deadnettle 100 100 100 100 100 — — — — — — — — — — — — — — — — — — — — — Foxtail, Giant 98 95 100 100 100 90 85 95 95 95 98 95 95 98 100 98 100 100 98 100 98 100 100 100 20 85 Foxtail, Green 95 70 98 80 70 90 90 90 90 90 90 100 95 100 98 98 95 98 95 98 100 100 100 90 30 100 Galium 85 85 60 90 80 — — — — — — — — — — — — — — — — — — — — — Goosegrass 90 98 100 100 100 95 35 95 90 85 80 90 80 98 100 100 98 98 100 98 98 98 100 98 65 95 Johnsongrass 70 80 100 80 100 65 80 100 90 100 65 100 100 25 100 55 100 100 — 100 100 100 100 95 0 98 Kochia 100 98 35 100 98 100 100 100 100 100 100 100 100 — 100 100 100 100 98 100 100 100 100 65 25 80 Lambsquarters 100 100 100 100 100 100 100 100 100 98 98 100 98 100 100 100 100 100 100 100 100 100 100 100 90 95 Morningglory 100 100 100 90 100 80 98 100 100 100 100 100 100 100 100 — 100 100 100 — 100 100 100 100 45 95 Nutsedge, Yellow 65 75 70 75 75 70 60 85 55 75 65 70 55 25 60 65 45 25 70 45 85 75 75 60 20 75 Oat, Wild 25 50 80 75 85 85 60 85 50 50 30 40 35 60 95 60 90 60 30 60 100 98 100 90 10 55 Pigweed 100 100 100 100 100 100 100 100 100 98 100 100 100 — 100 — 100 100 100 100 100 100 100 100 85 95 Ragweed 80 — — — — 98 100 100 98 90 85 98 95 98 100 98 100 100 100 100 100 100 100 95 70 90 Ryegrass, Italian 5 30 50 45 35 40 70 40 60 20 10 0 10 60 60 5 60 70 0 40 95 95 85 80 0 40 Soybean 100 98 100 100 100 98 100 100 100 100 98 100 98 100 100 100 100 100 98 100 100 100 100 100 70 95 Surinam Grass 85 90 98 95 70 95 90 65 75 85 95 98 90 100 100 — 100 100 75 100 100 100 100 90 10 85 Velvetleaf 100 100 100 100 100 100 100 98 100 98 98 100 85 100 100 100 100 100 100 100 100 100 100 100 85 90 Wheat 0 30 65 60 40 50 0 50 15 30 20 35 35 65 80 60 85 80 30 50 100 95 98 80 0 20 Windgrass 80 65 100 75 98 85 45 85 60 85 50 90 65 60 98 85 100 95 70 98 100 95 98 95 0 50 125 g ai/ha Compounds 3 4 7 8 9 10 11 12 14 24 26 27 29 33 34 36 37 38 39 40 42 44 45 46 47 48 49 50 Barley 0 0 0 5 20 0 10 0 5 50 0 10 0 0 30 20 0 0 0 10 0 5 5 0 10 10 0 5 Bermudagrass 70 85 65 95 98 90 100 98 80 100 60 100 90 98 95 100 98 100 85 100 95 95 95 90 98 98 95 100 Blackgrass 0 30 0 10 40 50 40 10 5 40 10 45 40 30 10 15 5 15 0 10 15 30 10 10 25 20 0 5 Bromegrass, Downy 0 50 5 10 40 10 45 20 50 70 20 20 40 10 50 45 15 85 0 70 15 80 45 10 50 50 0 20 Canarygrass 0 75 0 70 50 5 90 5 20 — 50 30 40 5 50 50 10 10 0 30 0 30 30 0 40 45 0 5 Chickweed 98 100 90 100 95 95 100 100 80 95 85 50 50 100 98 100 85 100 100 100 80 98 98 95 100 95 80 98 Cocklebur 85 100 65 100 35 95 100 100 90 98 95 95 95 95 85 — — — 95 — 85 90 70 80 95 98 80 90 Corn 10 50 0 75 75 45 80 45 45 85 40 50 50 10 45 65 60 75 45 85 20 80 60 60 80 85 5 25 Crabgrass, Large 80 100 45 90 85 75 100 80 85 95 50 60 55 90 95 95 85 98 85 100 85 95 75 75 90 95 80 95 Cupgrass, Woolly 20 100 50 90 80 70 90 70 80 95 85 70 85 70 90 95 75 95 85 98 25 85 75 25 90 90 55 80 Deadnettle — — — — — — — — — — — — — — — — — — — — — — — — — — — — Foxtail, Giant 60 98 55 100 95 80 98 98 80 90 70 90 90 85 95 98 95 100 95 100 75 95 95 80 98 95 70 95 Foxtail, Green 35 60 30 85 80 70 85 70 50 90 85 80 75 90 90 90 85 95 90 95 60 90 85 85 95 95 75 95 Galium — — — — — — — — — — — — — — — — — — — — — — — — — — — — Goosegrass 70 85 35 95 90 95 95 98 80 85 95 98 85 85 90 90 85 90 65 95 90 90 80 80 95 95 70 90 Johnsongrass — 95 0 98 85 60 90 60 80 70 50 45 40 35 95 85 60 95 90 75 40 90 98 70 98 80 10 65 Kochia 85 100 45 100 25 15 75 60 — 80 — 100 — 95 100 60 15 100 60 10 100 75 15 20 98 100 80 100 Lambsquarters 98 100 65 100 80 90 95 98 85 90 90 95 90 98 100 100 98 100 100 100 100 95 100 90 98 100 90 100 Morningglory 55 90 15 100 70 45 70 70 80 60 75 80 80 80 85 75 75 75 75 75 75 75 80 45 90 80 80 70 Nutsedge, Yellow 65 75 0 80 60 60 50 65 30 30 35 50 70 75 55 25 25 15 15 55 70 50 45 70 70 60 70 70 Oat, Wild 5 50 0 35 40 20 70 20 50 60 45 50 60 40 60 75 40 80 30 90 10 80 60 20 60 85 5 10 Pigweed 100 100 90 100 100 95 85 98 80 80 85 100 80 98 98 90 98 98 100 100 100 98 100 80 100 100 95 100 Ragweed 98 100 80 100 75 90 100 100 85 90 98 100 100 98 95 95 95 80 95 98 85 95 95 80 95 90 80 98 Ryegrass, Italian 5 15 0 30 30 0 40 5 5 40 10 5 40 40 20 10 5 60 5 0 10 10 35 5 30 30 0 0 Soybean 80 100 75 98 85 95 100 100 90 95 95 95 98 98 95 100 95 90 98 100 95 95 98 90 98 98 85 95 Surinam Grass 40 75 20 75 75 70 85 65 50 60 60 80 70 75 80 85 75 90 65 98 45 95 95 80 98 95 55 80 Velvetleaf 100 90 90 95 90 75 100 98 90 98 95 80 80 98 98 100 95 100 80 100 95 100 90 85 98 98 98 98 Wheat 10 50 10 35 30 0 40 0 0 30 5 10 10 5 35 5 0 40 5 30 5 30 15 0 5 10 15 5 Windgrass 0 60 5 30 60 30 85 45 30 60 40 50 30 30 50 80 50 85 5 80 70 85 70 15 80 90 5 60 125 g ai/ha Compounds 51 52 53 55 56 58 59 61 62 63 64 66 67 68 69 70 71 72 73 74 75 77 79 80 81 82 83 85 Barley 30 25 70 0 30 5 10 0 5 0 — 0 20 25 15 90 0 0 0 0 0 0 35 30 0 0 5 20 Bermudagrass 90 95 98 85 100 98 98 90 85 85 98 95 70 95 98 95 80 85 90 95 98 95 85 45 95 85 85 90 Blackgrass 50 25 40 5 20 20 40 0 30 35 5 10 5 0 0 35 0 0 10 25 0 0 30 5 30 5 0 35 Bromegrass, Downy 55 60 55 0 50 45 35 0 50 20 60 20 0 25 70 70 10 0 50 5 35 5 30 60 30 5 45 25 Canarygrass 60 65 90 0 40 80 50 0 0 0 40 0 0 35 25 85 5 0 5 0 0 0 35 50 10 15 25 55 Chickweed 85 95 98 80 98 90 98 95 75 80 98 95 95 98 98 98 95 90 95 95 98 95 95 100 98 98 98 95 Cocklebur 90 85 85 65 75 85 90 70 55 90 95 25 90 90 20 40 95 90 65 90 95 60 98 45 65 95 80 98 Corn 80 65 80 5 65 65 75 10 75 25 85 70 65 80 25 60 0 5 80 15 20 60 60 65 15 5 15 85 Crabgrass, Large 85 90 95 80 90 90 95 75 80 80 98 65 90 90 98 95 80 85 90 95 100 75 90 90 95 80 95 90 Cupgrass, Woolly 80 85 95 15 65 70 90 60 60 65 98 60 70 55 95 90 85 50 65 55 55 35 65 70 90 65 90 90 Deadnettle — — — — — — — — — — — — — — — — — — — — — — — — — — — — Foxtail, Giant 85 90 90 55 85 90 95 65 75 65 98 80 85 85 98 95 80 75 80 70 85 75 95 95 95 95 95 90 Foxtail, Green 95 98 100 80 98 98 70 60 80 70 100 90 80 85 100 98 70 90 90 80 90 80 80 95 95 85 98 95 Galium — — — — — — — — — — — — — — — — — — — — — — — — — — — — Goosegrass 85 85 80 65 75 85 95 65 65 70 85 70 65 85 85 85 90 65 75 80 95 75 70 80 70 80 80 80 Johnsongrass 85 90 95 10 85 98 100 10 0 10 100 65 5 75 100 80 98 40 70 10 20 10 70 10 75 80 100 95 Kochia 25 55 75 75 100 25 45 70 60 25 80 90 85 95 80 75 25 90 90 95 100 95 75 20 90 65 80 85 Lambsquarters 95 90 98 95 100 100 100 95 98 98 100 95 98 100 100 100 90 100 100 95 100 98 100 98 100 100 100 98 Morningglory 90 75 80 75 100 90 80 70 75 75 85 100 95 98 75 100 75 90 75 95 95 80 100 100 100 100 85 100 Nutsedge, Yellow 75 45 75 55 75 55 70 60 35 50 10 65 65 70 40 40 10 65 50 70 70 70 70 55 80 45 70 85 Oat, Wild 60 95 85 0 40 60 55 0 25 5 95 5 10 50 85 90 0 30 80 60 50 5 60 40 50 5 10 25 Pigweed 98 95 100 90 100 98 100 90 100 95 100 100 98 100 100 98 98 100 100 100 100 100 100 100 100 100 100 100 Ragweed 90 80 95 95 75 90 90 85 75 80 90 25 85 80 100 75 80 90 85 85 90 80 95 65 98 95 85 85 Ryegrass, Italian 10 55 40 0 50 30 70 0 50 0 0 5 5 15 50 50 0 10 60 20 40 5 50 5 45 5 0 35 Soybean 95 95 95 60 95 95 95 10 90 85 98 98 98 98 98 95 95 85 90 95 98 70 95 90 95 95 90 90 Surinam Grass 90 90 98 45 85 95 90 75 65 35 98 85 20 70 100 95 65 80 85 65 70 75 75 60 98 75 85 85 Velvetleaf 90 98 95 98 98 85 95 95 95 98 98 98 98 100 98 100 90 100 100 100 100 98 98 100 100 90 95 98 Wheat 10 35 30 5 0 0 10 0 5 0 30 0 25 5 10 35 0 10 40 30 10 10 35 20 25 0 0 20 Windgrass 60 90 85 0 60 60 60 0 35 40 95 70 5 65 80 90 45 60 90 80 70 20 65 70 60 20 15 80 125 g ai/ha Compounds 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100 102 107 108 109 111 113 117 118 119 120 121 Barley 60 0 40 10 10 30 0 5 5 0 0 0 10 10 30 30 25 0 5 5 5 0 0 5 5 5 Bermudagrass 95 98 80 95 85 95 85 85 98 75 95 95 85 80 75 85 95 100 90 100 95 95 98 98 98 100 Blackgrass 45 20 5 20 5 30 5 30 10 0 30 30 20 5 10 30 15 20 40 25 5 40 35 50 60 40 Bromegrass, Downy 35 60 45 5 10 5 20 0 0 0 5 5 5 25 15 10 10 5 5 5 80 15 30 60 60 80 Canarygrass 80 35 80 50 30 65 0 5 30 0 30 10 35 60 5 30 60 5 30 0 — 5 10 30 55 5 Chickweed 95 100 95 98 85 98 98 95 100 98 98 100 98 98 95 95 100 100 98 100 100 98 95 100 85 100 Cocklebur 95 100 95 65 100 95 98 95 60 100 98 100 100 100 95 100 100 100 100 100 98 98 85 80 25 85 Corn 80 75 65 98 45 45 45 50 70 25 65 60 55 65 20 65 75 50 60 55 80 25 20 60 50 55 Crabgrass, Large 98 95 98 95 75 98 98 80 90 75 85 85 80 95 75 85 90 75 75 80 95 95 80 95 95 95 Cupgrass, Woolly 95 75 90 65 50 98 65 65 65 65 85 70 75 80 70 75 75 70 60 75 95 95 75 98 100 100 Deadnettle — — — — — — — — — — — — — — — — — — — — — — — — — — Foxtail, Giant 98 85 95 90 75 98 90 80 85 75 80 85 85 95 80 80 85 75 80 65 90 80 85 95 85 98 Foxtail, Green 100 90 100 70 80 98 98 80 70 65 70 85 85 95 80 90 90 80 85 65 80 80 95 95 95 100 Galium — — — — — — — — — — — — — — — — — — — — — — — — — — Goosegrass 85 95 70 75 75 85 75 65 75 75 85 80 80 75 75 80 75 75 80 85 85 75 80 85 85 98 Johnsongrass 100 35 100 100 30 95 98 50 45 15 70 75 75 80 10 60 70 20 50 20 90 — 20 75 75 — Kochia 98 100 80 85 85 85 95 95 80 100 95 98 80 100 98 100 100 98 85 100 100 — 70 95 80 — Lambsquarters 100 100 100 98 100 100 100 95 100 98 100 100 100 100 98 100 100 100 100 100 98 100 100 100 98 100 Morningglory 90 65 95 90 100 98 100 95 100 100 100 100 100 100 100 100 100 100 100 100 100 80 70 95 80 25 Nutsedge, Yellow 75 70 70 70 70 75 70 70 60 85 85 80 70 70 15 75 75 80 75 80 75 25 65 65 65 45 Oat, Wild 60 65 70 20 10 45 5 0 5 0 25 5 20 40 30 40 20 0 30 0 45 30 10 95 80 98 Pigweed 100 — 100 100 100 100 100 98 100 100 98 100 100 100 98 95 100 100 100 100 100 — 100 100 100 100 Ragweed 95 98 95 95 85 95 75 85 65 95 95 100 80 80 75 85 95 95 95 98 98 90 95 95 75 90 Ryegrass, Italian 50 40 30 20 0 10 5 0 0 0 10 0 15 20 10 5 5 0 5 0 50 15 5 60 60 70 Soybean 98 100 98 98 98 95 98 95 95 98 75 95 98 100 100 95 100 65 98 95 98 95 95 60 95 95 Surinam Grass 98 — 95 80 70 98 70 70 65 45 75 80 85 75 65 75 80 65 65 70 90 — 75 95 100 100 Velvetleaf 100 100 95 98 100 100 100 95 75 100 98 100 95 100 70 100 100 100 100 100 98 95 98 100 98 100 Wheat 40 50 5 5 15 35 0 0 0 0 10 0 5 5 15 20 5 0 5 5 40 20 5 60 60 45 Windgrass 85 85 65 30 5 50 80 50 45 0 45 60 50 10 45 60 80 30 60 35 35 65 70 100 90 100 125 g ai/ha Compounds 122 123 126 127 128 129 130 131 140 141 146 147 152 155 156 157 160 162 164 169 173 181 184 186 187 189 Barley 50 25 15 35 0 0 0 0 0 5 15 0 85 45 60 30 35 50 30 0 35 50 60 5 40 15 Bermudagrass 85 90 90 98 98 95 90 85 85 85 100 95 98 98 95 100 90 100 98 100 100 100 100 95 100 65 Blackgrass 15 40 30 25 10 5 5 0 5 10 35 45 55 60 35 10 20 55 10 10 30 15 40 5 5 5 Bromegrass, Downy 50 10 30 20 40 15 35 0 5 10 10 5 60 35 35 60 50 45 85 90 40 60 50 30 35 5 Canarygrass 45 55 60 35 30 0 20 0 5 5 5 5 80 50 40 80 20 90 90 80 40 85 80 40 55 5 Chickweed 80 95 98 98 95 90 100 90 45 90 98 98 90 100 100 100 95 100 98 100 100 100 100 100 100 100 Cocklebur 85 100 80 95 100 98 95 100 65 95 — 90 98 98 75 100 100 100 100 100 100 100 100 100 100 100 Corn 25 75 55 25 60 60 80 20 25 45 20 25 65 40 45 95 50 80 45 55 60 95 85 30 75 35 Crabgrass, Large 85 85 85 90 95 85 95 80 80 80 85 85 95 80 65 98 95 98 98 100 95 100 100 85 100 95 Cupgrass, Woolly 75 75 85 85 90 85 85 65 65 65 65 80 98 65 55 98 85 100 98 100 100 100 100 80 85 75 Deadnettle — — — — — — — — — — — — — — — — — — — — — — 100 100 — 100 Foxtail, Giant 80 80 85 85 98 90 98 80 80 80 95 85 95 90 85 100 75 98 98 100 100 100 100 95 100 90 Foxtail, Green 85 85 90 90 95 90 95 95 85 90 80 80 98 80 85 85 70 98 98 95 90 95 85 85 98 90 Galium — — — — — — — — — — — — — — — — — — — — — — 60 70 55 85 Goosegrass 70 80 75 75 98 90 95 75 70 75 95 80 95 85 70 98 90 90 98 100 95 100 100 98 100 90 Johnsongrass 75 75 85 80 85 70 80 50 35 50 70 60 95 65 45 100 65 100 95 65 95 100 100 75 100 65 Kochia 45 80 25 100 95 95 100 75 10 85 85 80 95 100 20 10 100 75 100 100 98 100 5 100 70 98 Lambsquarters 90 98 85 90 100 95 100 98 75 98 100 98 98 100 95 100 98 98 100 100 100 100 100 100 100 100 Morningglory 85 100 100 90 90 90 100 75 65 60 85 65 75 100 100 95 100 90 98 100 80 100 100 100 100 100 Nutsedge, Yellow 75 75 80 75 60 60 35 45 65 60 20 70 80 70 70 40 80 75 70 55 60 80 45 75 65 55 Oat, Wild 35 30 35 25 60 20 40 0 10 15 50 20 80 60 35 60 50 45 85 85 70 90 80 20 45 10 Pigweed 98 100 98 95 98 98 100 100 75 95 100 100 100 100 98 90 100 100 100 100 100 100 75 100 100 100 Ragweed 75 95 85 98 95 95 98 95 65 85 98 90 95 90 75 100 98 100 98 100 90 100 — 100 100 75 Ryegrass, Italian 40 5 5 5 5 0 0 0 0 0 10 30 45 40 20 30 35 80 20 10 30 60 45 0 10 5 Soybean 80 85 85 98 98 98 98 98 75 75 98 65 98 100 98 100 98 100 100 95 95 100 100 100 100 98 Surinam Grass 90 85 85 85 85 85 80 65 55 70 75 75 90 65 60 98 60 75 95 — — 95 100 — — 80 Velvetleaf 98 95 95 100 95 95 98 98 80 98 98 95 100 100 95 100 100 95 80 100 100 100 100 100 100 100 Wheat 50 15 35 25 0 0 5 0 10 5 15 5 85 40 35 20 40 35 35 5 40 50 55 0 5 0 Windgrass 50 80 40 55 70 80 75 5 5 40 60 55 85 70 55 70 60 60 75 55 70 60 90 50 65 60 125 g ai/ha 62 g ai/ha Compounds Compounds 190 191 193 197 217 218 219 220 225 226 227 228 229 233 235 236 237 238 239 240 243 244 245 255 1 2 Barley 40 50 50 10 10 35 30 10 40 30 5 40 5 10 40 0 40 35 5 15 95 90 85 35 0 20 Bermudagrass 100 100 100 100 98 95 100 98 85 85 85 90 85 100 100 98 100 100 100 100 100 100 100 95 50 85 Blackgrass 35 50 40 10 30 5 55 30 15 40 5 50 5 30 70 30 70 60 30 65 85 65 80 10 0 30 Bromegrass, Downy 35 50 40 30 40 20 80 15 85 5 0 10 20 50 50 10 90 50 5 25 95 75 95 80 0 60 Canarygrass 25 60 25 40 20 0 55 10 85 50 5 5 50 10 30 0 50 30 0 30 100 98 100 50 0 50 Chickweed 100 98 100 100 100 100 100 98 95 85 80 100 90 100 100 100 100 100 98 100 100 98 100 100 60 90 Cocklebur 95 98 100 100 98 — — — 100 100 95 100 100 100 — 100 — — 100 — — — — — 65 90 Corn 40 75 40 45 25 75 75 55 70 98 75 85 85 85 100 70 100 95 45 100 100 95 100 85 0 25 Crabgrass, Large 80 100 98 98 90 70 95 85 95 95 85 98 90 98 98 98 100 98 95 100 100 100 100 90 50 85 Cupgrass, Woolly 80 90 95 90 45 60 95 65 85 85 90 95 80 100 100 95 100 100 95 100 100 100 100 95 0 80 Deadnettle 100 100 100 100 — — — — — — — — — — — — — — — — — — — — — — Foxtail, Giant 90 100 95 98 85 65 80 55 85 95 90 95 80 98 100 95 98 100 90 100 98 95 100 98 15 85 Foxtail, Green 45 80 60 50 85 90 90 80 98 90 90 98 80 95 95 98 95 98 90 95 100 98 100 90 10 90 Galium 60 60 90 — — — — — — — — — — — — — — — — — — — — — — — Goosegrass 80 100 98 100 85 15 95 85 95 85 75 85 70 98 98 95 98 98 98 98 98 98 100 95 60 90 Johnsongrass 75 100 70 95 60 55 98 80 75 100 60 95 100 25 100 20 100 98 60 100 100 100 100 90 0 90 Kochia 98 25 100 95 100 100 98 75 15 100 85 100 80 — 100 100 100 100 98 100 100 100 100 15 20 75 Lambsquarters 100 98 98 100 100 100 100 100 98 95 98 100 95 100 100 100 100 100 100 100 100 100 100 98 75 90 Morningglory 85 90 65 100 80 80 100 98 95 100 100 100 100 98 100 95 100 100 100 — 100 100 100 85 20 80 Nutsedge, Yellow 65 55 75 65 70 15 70 25 25 70 65 60 40 25 55 15 45 20 65 20 70 65 70 15 20 60 Oat, Wild 40 70 70 70 50 60 80 30 85 50 10 15 10 45 85 20 60 50 5 45 85 95 85 85 5 45 Pigweed 100 98 100 98 100 100 100 100 98 98 100 100 95 — 100 98 100 100 98 100 100 100 100 98 80 90 Ragweed — — — — 85 98 98 98 90 85 70 95 80 98 100 98 100 100 100 100 98 98 100 95 70 80 Ryegrass, Italian 20 50 40 30 40 60 40 30 40 5 5 0 0 50 55 0 60 25 0 40 85 80 70 30 0 40 Soybean 95 100 98 100 95 100 100 90 98 100 95 100 98 100 100 98 100 100 98 95 100 100 100 100 65 90 Surinam Grass 75 90 80 65 80 85 35 60 85 80 80 95 80 100 100 75 100 100 45 100 100 100 100 90 0 75 Velvetleaf 100 90 100 100 100 100 95 95 90 90 98 100 85 95 100 100 100 100 100 85 100 100 100 98 75 85 Wheat 30 55 60 5 50 0 50 0 55 25 10 20 5 60 80 30 85 80 5 50 95 85 95 50 0 10 Windgrass 65 85 70 50 80 45 60 40 80 70 40 80 50 60 95 70 98 85 30 98 98 80 95 80 0 15 62 g ai/ha Compounds 3 4 7 8 9 10 11 12 14 24 26 27 29 33 34 36 37 38 39 40 42 44 45 46 47 48 49 50 51 52 53 55 56 Barley 0 0 0 0 0 0 10 0 0 5 0 0 0 0 30 10 0 0 0 0 0 0 5 0 10 5 0 0 25 0 50 0 10 Bermudagrass 25 85 45 85 95 75 100 85 70 95 50 90 90 95 95 98 90 100 60 100 75 95 85 85 — 95 85 100 90 95 95 80 85 Blackgrass 0 20 0 10 0 0 5 10 0 10 0 5 20 15 5 5 0 15 0 10 10 10 5 5 20 5 0 5 30 5 30 0 10 Bromegrass, Downy 0 15 0 5 30 0 35 10 30 50 15 5 10 5 50 30 10 70 0 50 5 70 20 5 40 25 0 5 50 55 50 0 45 Canarygrass 0 20 0 50 25 0 50 5 20 40 30 10 20 0 50 45 5 10 0 20 0 20 10 0 30 30 0 0 60 50 80 0 30 Chickweed 98 100 80 100 85 95 98 100 — 90 50 45 50 98 75 98 80 90 100 100 70 95 85 95 98 90 75 80 80 95 98 75 95 Cocklebur 80 100 45 100 0 90 100 98 90 98 80 95 95 90 25 — — — 75 — 45 80 50 80 — 95 80 85 85 85 85 60 55 Corn 0 25 0 65 45 15 75 30 40 50 35 40 35 10 0 55 15 70 45 80 10 80 45 35 — 70 5 10 80 45 80 5 65 Crabgrass, Large 70 85 45 85 80 70 85 75 55 75 50 50 50 85 85 95 75 90 80 98 75 90 75 65 85 85 75 85 85 90 95 75 85 Cupgrass, Woolly 15 95 50 80 75 70 75 60 80 80 40 60 85 65 80 90 65 90 85 95 20 80 75 20 90 80 50 75 75 75 90 10 45 Deadnettle — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — Foxtail, Giant 45 98 55 100 85 75 85 90 70 85 60 85 90 80 90 95 85 98 85 100 65 95 90 80 98 85 60 85 80 80 85 30 80 Foxtail, Green 10 40 20 70 40 25 60 60 45 40 40 80 75 85 90 90 65 90 80 95 55 90 80 60 90 95 50 80 95 98 100 40 85 Galium — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — Goosegrass 50 75 25 85 85 75 85 85 80 85 90 90 85 75 80 85 85 85 55 90 85 90 75 75 95 85 70 80 80 80 80 60 75 Johnsongrass 0 80 0 98 70 55 70 60 80 60 50 45 20 35 90 75 40 75 65 — 0 70 90 50 — 80 0 10 75 85 95 0 80 Kochia 80 100 45 100 15 15 25 20 — 70 — — — 80 95 0 0 80 45 0 100 75 0 0 95 98 65 100 20 25 65 65 95 Lambsquarters 95 100 65 100 80 80 70 85 85 90 90 95 85 98 98 100 98 95 95 100 95 95 98 85 98 95 80 98 90 85 95 80 98 Morningglory 20 85 15 90 45 45 15 60 70 60 50 80 70 60 80 70 70 70 75 — 70 70 75 30 80 70 80 25 80 45 75 60 — Nutsedge, Yellow 45 65 0 70 25 55 35 55 30 30 30 40 50 50 25 20 15 0 0 35 60 50 10 70 65 45 65 70 65 25 65 10 70 Oat, Wild 0 50 0 15 5 5 50 5 40 50 40 50 50 15 50 75 10 75 20 85 10 80 55 5 60 50 5 5 60 90 70 0 20 Pigweed 90 100 75 100 85 85 80 95 80 80 80 98 65 95 90 85 85 98 100 98 95 95 98 75 98 85 90 98 95 90 95 85 98 Ragweed 85 100 65 100 75 80 100 100 80 80 85 98 85 95 85 90 80 80 85 98 75 95 85 75 90 85 80 90 80 80 85 80 55 Ryegrass, Italian 0 10 0 20 0 0 10 0 5 5 0 5 20 10 10 5 0 50 5 0 5 5 30 5 30 5 0 0 0 45 5 0 0 Soybean 70 100 65 98 75 95 100 100 85 95 95 95 95 98 95 98 80 85 95 100 90 95 95 80 95 95 65 85 90 95 95 60 85 Surinam Grass 25 70 10 65 65 70 70 55 50 55 40 70 50 65 75 85 70 85 65 95 40 95 75 75 95 85 30 75 85 85 95 15 80 Velvetleaf 100 75 80 80 85 70 95 85 90 90 70 60 55 90 95 100 80 100 80 100 80 98 80 80 85 85 95 98 85 98 85 98 90 Wheat 0 5 0 30 5 0 35 0 0 10 0 5 0 0 10 5 0 20 5 20 0 10 15 0 0 0 5 5 10 25 25 0 0 Windgrass 0 55 5 20 55 10 85 40 30 30 30 10 10 25 40 70 30 80 0 70 60 70 60 10 — 80 0 50 60 80 80 0 40 62 g ai/ha Compounds 58 59 61 62 63 64 66 67 68 69 70 71 72 73 74 75 77 79 80 81 82 83 85 86 87 88 89 90 91 Barley 5 0 0 5 0 — 0 5 0 5 30 0 0 0 0 0 0 30 30 0 0 5 10 40 0 30 5 5 30 Bermudagrass 85 90 90 80 85 95 70 70 75 98 85 75 80 80 80 98 90 80 40 85 85 75 85 90 90 80 85 80 95 Blackgrass 10 35 0 30 35 0 10 0 0 0 35 0 0 10 0 0 0 15 0 10 0 0 35 30 5 5 15 5 20 Bromegrass, Downy 40 30 0 45 20 45 10 0 5 55 50 5 0 45 5 20 5 10 60 5 0 45 5 10 50 45 0 5 5 Canarygrass 60 5 0 0 0 40 0 0 0 0 80 5 0 0 0 0 0 30 50 5 0 20 40 20 30 70 35 10 55 Chickweed 80 98 80 70 65 98 85 95 90 98 90 90 85 80 85 90 85 95 98 98 90 90 95 95 100 85 80 80 95 Cocklebur 85 85 65 55 80 95 10 75 75 0 0 65 80 45 85 80 0 98 10 55 90 80 95 95 100 90 60 90 65 Corn 45 0 0 70 20 85 55 10 15 10 35 0 0 80 0 0 5 45 35 10 5 5 70 60 55 65 95 25 35 Crabgrass, Large 80 85 65 75 75 90 55 80 90 95 90 75 80 85 80 98 60 85 80 95 75 85 90 98 85 98 95 75 95 Cupgrass, Woolly 65 75 55 55 60 95 40 70 10 95 65 45 45 65 10 55 20 40 70 75 55 85 85 85 75 80 50 45 85 Deadnettle — — — — — — — — — — — — — — — — — — — — — — — — — — — — — Foxtail, Giant 85 90 65 65 65 95 75 80 80 98 85 75 70 75 55 80 75 75 90 85 80 95 80 95 80 95 85 70 98 Foxtail, Green 90 70 55 70 70 85 85 80 85 98 85 60 70 90 20 85 80 60 95 85 60 95 95 95 80 98 70 65 85 Galium — — — — — — — — — — — — — — — — — — — — — — — — — — — — — Goosegrass 75 80 50 65 70 80 65 55 70 80 85 75 65 75 75 80 75 65 75 70 75 80 70 75 80 70 65 60 75 Johnsongrass 85 75 0 0 10 98 60 0 10 100 70 75 10 65 0 10 0 65 0 10 80 100 95 98 25 100 90 25 90 Kochia 10 10 25 25 25 55 85 80 90 70 65 0 85 80 75 95 80 75 20 80 60 75 85 85 100 75 75 85 80 Lambsquarters 95 98 95 95 95 100 95 95 98 100 98 85 100 98 95 100 98 98 95 98 95 98 98 100 98 98 98 95 100 Morningglory 80 50 70 15 70 80 100 90 85 70 100 65 85 50 85 90 75 95 100 90 100 75 100 80 45 90 85 95 90 Nutsedge, Yellow 40 60 60 25 20 10 45 65 10 10 15 10 65 20 20 65 60 60 15 80 15 20 85 70 60 65 55 65 65 Oat, Wild 60 40 0 10 0 90 0 5 20 80 70 0 — 80 20 20 5 45 30 35 0 10 25 50 60 55 10 5 30 Pigweed 95 100 85 98 95 100 98 98 95 100 98 85 100 98 98 100 98 100 100 100 98 90 100 100 98 100 98 98 100 Ragweed 85 80 80 75 75 85 10 80 80 90 70 80 80 80 75 85 75 85 60 80 80 80 85 90 95 80 85 75 85 Ryegrass, Italian 0 50 0 5 0 0 0 5 5 50 10 0 0 45 20 15 5 20 0 5 0 0 10 30 10 5 5 0 5 Soybean 85 95 0 80 75 98 95 90 95 90 75 70 80 85 75 95 50 90 80 95 90 90 85 95 98 90 90 98 85 Surinam Grass 80 80 65 45 25 95 70 20 55 90 65 55 80 85 45 50 65 45 45 90 65 75 85 95 75 95 75 65 98 Velvetleaf 75 90 80 95 98 98 90 95 100 98 80 85 100 100 100 100 98 98 100 100 90 90 98 100 100 90 95 98 100 Wheat 0 5 0 0 0 15 — 5 5 5 20 0 5 35 5 0 5 25 10 20 0 0 5 35 35 5 5 10 10 Windgrass 50 60 0 35 30 90 60 0 50 60 85 10 20 80 60 50 10 65 60 50 5 10 70 60 60 60 5 5 40 62 g ai/ha Compounds 92 93 94 95 96 97 98 99 100 102 107 108 109 111 113 117 118 119 120 121 122 123 126 127 128 129 Barley 0 0 0 0 0 0 5 5 20 10 5 0 0 0 5 0 0 0 5 5 10 10 5 20 0 0 Bermudagrass 80 75 80 75 95 95 80 75 70 85 80 90 85 100 90 90 95 98 95 98 80 85 85 95 85 80 Blackgrass 0 5 10 0 20 20 5 0 5 5 5 5 5 5 0 10 10 20 30 40 5 20 25 20 5 5 Bromegrass, Downy 5 0 0 0 0 0 5 5 10 10 5 0 0 0 60 10 5 30 60 50 5 5 15 10 35 10 Canarygrass 0 0 5 0 5 10 20 60 5 20 15 5 0 0 90 0 0 5 30 5 35 40 40 10 10 0 Chickweed 95 80 100 85 95 100 80 98 75 80 100 100 98 100 98 95 95 80 75 100 70 75 80 75 90 85 Cocklebur 80 90 45 95 95 100 100 100 85 95 100 95 98 98 95 75 40 10 15 45 45 80 65 95 98 98 Corn 35 45 55 0 60 40 35 65 10 15 65 35 15 45 60 15 0 45 20 55 15 70 30 25 50 35 Crabgrass, Large 90 80 75 65 80 80 75 85 60 80 85 70 75 75 90 80 75 85 85 90 75 80 80 85 85 80 Cupgrass, Woolly 25 45 65 55 75 60 70 75 65 75 65 60 60 50 85 85 70 98 75 100 70 45 75 75 90 85 Deadnettle — — — — — — — — — — — — — — — — — — — — — — — — — — Foxtail, Giant 75 80 75 65 70 75 75 80 75 75 80 60 75 65 85 75 80 85 80 98 75 75 80 85 95 85 Foxtail, Green 80 60 60 50 65 85 85 90 70 90 75 30 80 60 80 70 85 90 95 90 85 60 80 85 95 90 Galium — — — — — — — — — — — — — — — — — — — — — — — — — — Goosegrass 70 65 70 75 70 70 75 75 70 70 75 70 75 70 75 75 65 75 80 98 65 65 70 75 95 85 Johnsongrass 85 10 15 10 45 55 70 75 5 25 70 20 30 15 85 20 10 40 25 70 65 65 65 70 70 45 Kochia 90 85 55 100 85 90 70 80 95 70 98 95 75 100 100 50 65 75 40 100 0 65 25 98 85 95 Lambsquarters 98 95 95 98 98 100 98 100 98 98 100 98 98 98 98 98 98 100 85 100 65 95 85 85 98 95 Morningglory 95 80 75 100 95 100 85 100 100 100 100 90 98 100 100 75 60 60 50 20 75 98 85 80 80 90 Nutsedge, Yellow 65 60 20 75 70 75 60 70 5 65 75 75 65 75 75 0 45 50 35 45 70 75 75 70 35 35 Oat, Wild 5 0 5 0 5 5 20 20 10 15 5 0 0 0 40 10 5 60 80 90 30 5 10 10 50 5 Pigweed 100 95 100 98 95 100 100 100 98 70 100 98 100 100 100 98 100 98 98 100 90 98 95 95 98 95 Ragweed 60 75 45 80 80 98 75 80 70 80 85 85 95 95 95 75 85 75 75 85 60 85 75 85 85 95 Ryegrass, Italian 0 0 0 0 5 0 5 0 5 0 0 0 0 0 45 10 5 30 40 40 10 5 5 5 0 0 Soybean 98 80 80 98 75 80 98 100 98 85 98 55 95 80 98 80 90 50 80 90 75 75 75 98 98 98 Surinam Grass 65 65 60 45 75 75 75 70 65 75 75 60 65 — 85 75 — 85 85 100 75 75 80 75 80 85 Velvetleaf 100 90 70 95 98 100 95 100 70 100 100 100 98 98 95 85 75 80 95 98 90 90 90 95 95 95 Wheat 0 0 0 0 5 0 5 5 5 10 5 0 5 0 15 5 5 40 40 45 30 15 15 10 0 0 Windgrass 50 10 40 0 10 50 20 5 40 10 40 10 40 30 30 45 60 85 80 98 30 60 10 50 65 60 62 g ai/ha Compounds 130 131 140 141 146 147 152 155 156 157 159 160 162 164 169 173 181 184 186 187 189 190 191 193 197 217 Barley 0 0 0 0 0 0 45 30 45 15 50 30 35 5 0 20 40 40 5 5 5 5 50 0 5 5 Bermudagrass 90 75 75 85 90 90 95 98 90 90 100 75 95 98 75 98 100 100 80 85 15 100 100 100 100 85 Blackgrass 5 0 0 5 30 40 35 35 5 5 25 10 40 5 5 10 5 35 0 0 0 30 45 15 10 5 Bromegrass, Downy 15 0 5 5 5 5 55 30 10 40 50 5 30 80 40 25 50 50 25 30 5 30 40 30 15 15 Canarygrass 20 0 0 0 0 0 45 35 30 70 90 20 50 85 80 35 80 50 25 35 0 5 50 5 30 20 Chickweed 98 80 10 85 95 90 65 100 98 100 100 95 100 90 100 95 100 100 98 100 100 100 98 98 100 95 Cocklebur 95 98 15 65 25 75 80 55 40 100 100 100 100 100 100 65 100 100 100 100 70 90 98 95 100 98 Corn 60 10 5 45 5 15 45 25 10 80 75 40 75 25 55 25 85 80 10 65 20 0 75 15 35 10 Crabgrass, Large 85 75 65 75 75 75 85 75 55 95 95 90 90 98 95 80 100 100 85 98 75 65 100 90 85 85 Cupgrass, Woolly 85 60 50 65 65 70 98 45 50 85 85 65 100 85 98 95 85 100 75 85 70 80 90 85 85 45 Deadnettle — — — — — — — — — — — — — — — — — 100 98 95 98 98 100 100 100 — Foxtail, Giant 90 75 75 75 85 80 85 80 80 98 95 75 95 98 98 98 98 100 80 98 75 85 100 85 95 75 Foxtail, Green 90 90 60 75 55 65 75 50 60 85 98 55 98 98 85 70 85 60 80 95 80 40 55 50 30 60 Galium — — — — — — — — — — — — — — — — — 50 40 50 60 50 40 — 75 — Goosegrass 85 65 65 75 90 70 85 80 70 95 90 85 70 98 95 90 98 100 95 98 80 75 98 95 98 80 Johnsongrass 60 25 15 15 45 40 90 40 45 100 60 55 98 85 65 80 100 100 70 100 55 65 100 65 85 60 Kochia 85 60 10 65 45 75 65 100 10 0 45 100 45 100 100 65 95 0 85 50 90 10 10 80 80 98 Lambsquarters 100 95 60 80 98 95 95 100 85 98 100 98 95 98 100 98 100 100 98 100 98 98 80 98 100 100 Morningglory 95 70 60 60 15 50 75 85 80 95 65 98 80 95 95 80 100 95 100 95 100 40 65 60 100 75 Nutsedge, Yellow 20 25 45 10 10 60 75 45 60 40 60 75 60 45 20 45 65 40 65 55 40 45 40 65 55 60 Oat, Wild 30 0 5 10 20 10 45 40 35 50 80 30 40 40 30 50 75 80 5 30 10 0 60 50 40 40 Pigweed 98 95 70 75 98 95 98 100 95 75 98 100 100 98 100 90 100 70 100 100 100 75 85 95 90 100 Ragweed 90 85 45 75 80 75 80 70 65 100 90 95 95 98 100 70 100 — 90 98 70 — — — — 80 Ryegrass, Italian 0 0 0 0 5 5 30 30 5 20 40 5 45 5 0 10 40 40 0 0 0 0 40 40 0 30 Soybean 98 95 60 70 85 60 70 95 90 98 95 98 100 95 95 95 100 100 95 100 98 80 95 98 100 85 Surinam Grass 80 60 50 65 65 65 85 55 60 90 75 55 70 95 — — 80 90 — 85 70 60 85 65 55 80 Velvetleaf 95 85 65 95 85 80 95 100 80 100 100 100 85 70 100 100 100 98 70 95 90 100 80 100 80 98 Wheat 5 0 5 5 0 5 50 30 30 10 55 30 30 15 0 35 45 45 0 0 0 5 40 35 0 45 Windgrass 65 0 5 35 50 50 70 55 50 65 60 30 45 40 30 65 50 80 30 50 40 50 85 70 50 50 62 g ai/ha 31 g ai/ha Compounds Compounds 218 219 220 225 226 227 228 229 233 235 236 237 238 239 240 243 244 245 255 1 2 3 4 7 8 9 10 11 Barley 30 25 10 35 30 5 5 0 0 30 0 15 30 0 5 90 65 85 35 0 10 0 0 0 0 0 0 0 Bermudagrass 80 98 95 85 80 75 85 80 95 98 98 98 98 100 100 98 100 100 95 40 80 15 15 35 60 90 70 80 Blackgrass 0 55 20 5 30 0 35 0 30 60 5 70 60 5 50 80 60 70 5 0 10 0 10 0 5 0 0 5 Bromegrass, Downy 15 50 10 70 0 0 5 15 40 30 5 45 40 5 20 70 50 95 60 0 35 0 10 0 5 5 0 20 Canarygrass 0 55 10 85 30 0 0 15 5 30 0 40 25 0 5 98 95 95 50 0 40 0 10 0 20 5 0 50 Chickweed 100 100 95 40 75 75 100 85 95 100 100 98 90 98 98 100 95 85 98 55 75 90 100 60 98 20 90 80 Cocklebur — — — 100 98 80 98 90 100 — 100 — — 100 — — — — — 65 80 65 100 45 100 0 70 90 Corn 10 60 50 50 80 75 85 80 50 100 60 98 80 45 95 95 90 100 75 0 15 0 10 0 15 15 15 70 Crabgrass, Large 45 95 75 85 85 80 98 90 90 98 90 98 98 90 98 100 100 100 85 40 80 60 70 30 70 70 65 80 Cupgrass, Woolly 45 85 60 75 80 75 95 75 85 100 85 100 100 95 100 95 100 100 95 0 75 0 75 0 75 70 60 55 Deadnettle — — — — — — — — — — — — — — — — — — — — — — — — — — — — Foxtail, Giant 55 70 50 80 90 80 85 80 95 100 80 98 100 85 100 95 95 100 98 0 85 15 80 20 98 75 70 75 Foxtail, Green 85 80 65 98 80 90 90 80 90 90 95 90 95 85 90 98 98 98 90 5 75 5 40 5 40 35 10 60 Galium — — — — — — — — — — — — — — — — — — — — — — — — — — — — Goosegrass 10 95 85 90 80 75 80 70 95 98 90 98 98 98 98 95 95 98 90 60 80 15 25 20 80 60 45 65 Johnsongrass — 60 65 75 85 60 75 100 5 80 15 100 — 20 100 100 95 100 85 0 85 0 45 0 80 60 0 65 Kochia 85 98 65 10 85 75 100 70 85 100 98 80 98 98 98 95 90 100 15 15 60 65 80 0 85 10 10 25 Lambsquarters 98 100 100 85 90 98 98 95 98 100 100 100 100 98 100 100 100 100 95 70 90 85 98 0 95 75 80 50 Morningglory 70 85 65 95 98 100 100 100 80 98 95 95 — — — 100 95 100 85 0 70 15 60 15 75 45 0 15 Nutsedge, Yellow 15 55 25 25 65 45 45 20 5 45 15 35 20 30 15 65 50 45 15 15 45 15 55 0 65 20 15 25 Oat, Wild 45 70 20 50 30 0 5 5 35 50 0 55 35 5 40 85 70 85 80 5 30 0 30 0 10 0 0 50 Pigweed 100 100 100 95 85 90 100 95 98 100 85 98 100 98 100 100 100 98 98 65 85 75 100 75 98 80 85 65 Ragweed 95 98 95 80 85 70 80 80 85 100 95 98 100 98 98 95 98 98 90 60 70 80 100 50 90 70 75 100 Ryegrass, Italian 40 25 5 35 0 0 0 0 45 30 0 50 25 0 15 85 60 50 30 0 0 0 10 0 20 0 0 10 Soybean 100 98 85 95 98 65 98 98 98 100 98 100 100 95 95 98 100 98 95 50 80 65 95 60 98 70 95 100 Surinam Grass 80 25 60 75 75 70 85 70 85 90 70 98 100 35 98 95 95 100 80 0 70 15 60 0 60 55 60 60 Velvetleaf 100 90 90 90 85 80 100 75 85 100 100 90 90 100 85 100 100 100 98 55 85 95 70 70 75 85 70 80 Wheat 0 50 0 40 15 0 5 0 30 80 10 70 45 0 35 95 80 95 40 0 5 0 5 0 25 0 0 30 Windgrass 20 40 40 55 50 30 50 40 55 95 50 90 70 30 80 90 70 70 80 0 10 0 50 5 5 50 5 40 31 g ai/ha Compounds 12 14 24 26 27 29 33 34 36 37 38 39 40 42 44 45 46 47 48 49 50 51 52 53 55 56 58 59 61 62 63 64 66 67 68 69 70 Barley 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 5 0 5 5 0 0 5 0 0 0 0 5 0 0 0 0 15 0 0 0 5 10 Bermudagrass 65 70 85 40 70 85 75 75 90 85 98 50 — 70 80 80 80 85 85 75 90 80 85 90 80 75 85 — 75 — — 95 70 35 75 98 75 Blackgrass 10 0 5 0 0 10 10 0 5 0 5 0 0 5 0 5 0 5 0 0 5 0 5 20 0 0 5 10 0 15 30 0 5 0 0 0 30 Bromegrass, Downy 5 10 25 10 5 5 5 40 30 0 50 0 45 0 40 10 0 35 10 0 0 50 50 35 0 35 40 5 0 30 10 25 5 0 5 40 10 Canarygrass 0 10 40 20 10 10 0 5 40 0 10 0 20 0 20 10 0 20 30 0 0 60 0 40 0 0 60 5 0 0 0 40 0 0 0 0 50 Chickweed 100 — 80 40 40 50 80 50 85 80 85 98 100 60 90 75 80 85 85 75 80 80 95 85 65 90 70 85 80 70 60 98 80 90 85 98 80 Cocklebur 70 80 90 80 90 85 85 0 — — — 75 — 0 80 10 75 95 95 65 85 85 75 80 45 5 85 85 0 25 65 90 10 75 25 0 0 Corn 25 10 30 35 35 20 0 0 50 0 55 25 80 0 75 10 20 65 65 5 5 75 30 55 0 45 0 — 0 70 — 80 25 5 0 5 15 Crabgrass, Large 65 50 70 40 50 45 75 80 90 70 90 75 85 70 85 65 60 85 85 75 75 80 85 85 60 75 75 80 65 55 70 85 50 75 75 95 80 Cupgrass, Woolly 55 50 80 40 60 80 65 80 85 55 80 65 90 15 80 70 10 85 80 50 70 75 70 65 10 15 65 75 55 55 50 75 40 60 10 90 45 Deadnettle — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — Foxtail, Giant 75 50 70 60 65 80 75 85 95 70 95 75 100 45 95 75 70 90 85 45 75 80 80 80 25 75 75 75 55 55 60 90 65 75 65 95 75 Foxtail, Green 40 45 40 35 80 60 50 70 85 60 85 80 90 50 90 50 45 80 85 50 80 85 95 95 30 80 75 50 50 40 60 70 80 10 40 95 80 Galium — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — Goosegrass 70 80 85 60 90 80 70 75 85 80 80 40 85 70 85 75 75 90 85 65 75 75 75 75 45 65 70 75 40 65 70 80 65 55 65 75 75 Johnsongrass 55 45 60 35 40 20 15 75 65 0 70 65 — 0 70 60 40 85 45 0 0 75 75 55 0 55 50 — 0 0 — 90 45 0 10 98 65 Kochia 20 — 70 — — — 10 85 0 0 65 20 0 80 75 0 0 95 98 55 95 20 20 45 20 90 0 — 5 10 10 50 80 75 70 60 65 Lambsquarters 80 85 90 80 90 85 95 95 98 95 90 95 100 90 90 95 80 98 85 70 98 75 85 90 80 98 95 95 85 85 — 95 95 80 95 100 85 Morningglory 15 70 50 50 50 60 60 60 60 60 65 65 70 45 60 75 30 75 70 65 10 75 10 55 55 — 65 — 45 — — 80 98 80 80 70 98 Nutsedge, Yellow 15 20 20 30 30 40 40 5 10 10 0 0 20 55 40 10 65 65 40 65 70 60 20 20 10 20 25 45 20 15 20 0 25 60 0 5 10 Oat, Wild 0 30 40 40 45 40 10 40 60 0 55 10 85 5 50 35 0 40 40 0 5 60 90 50 0 5 45 30 0 5 0 60 0 0 5 60 55 Pigweed 95 80 70 50 98 60 90 70 85 80 95 98 90 85 75 85 75 98 85 80 80 85 85 85 80 98 80 — 80 98 85 98 98 98 85 98 85 Ragweed 100 80 70 70 85 80 90 75 90 80 75 85 98 70 85 80 70 85 85 75 80 80 75 80 70 55 80 75 75 70 70 85 0 75 75 90 60 Ryegrass, Italian 0 0 0 0 0 5 5 10 0 0 35 0 0 0 5 30 0 0 0 0 0 0 40 0 0 0 0 5 0 0 0 0 0 0 5 30 10 Soybean 98 80 85 95 95 85 95 85 90 75 85 95 100 70 95 80 75 95 95 55 85 85 80 90 25 85 85 90 0 75 75 85 95 80 80 80 75 Surinam Grass 25 40 50 30 50 50 45 70 75 60 70 60 85 40 85 70 45 85 70 15 65 80 75 85 10 75 70 75 20 20 10 85 65 10 25 85 65 Velvetleaf 80 85 75 70 50 50 80 80 98 75 95 75 98 80 95 70 75 80 85 90 90 80 95 85 90 85 75 85 80 85 95 85 85 90 95 95 75 Wheat 0 0 5 0 0 0 0 0 5 0 0 5 0 0 5 10 0 0 0 0 0 5 15 20 0 0 0 0 0 0 0 10 0 5 5 5 5 Windgrass 10 5 20 10 10 5 10 10 50 5 70 0 70 10 65 30 10 60 70 0 10 50 60 60 0 30 35 20 0 30 10 70 60 0 40 60 80 31 g ai/ha Compounds 71 72 73 74 75 77 79 80 81 82 83 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100 102 107 108 Barley 0 0 0 0 0 0 5 15 0 0 0 5 30 0 30 0 0 0 0 0 0 0 0 0 0 5 5 0 0 0 Bermudagrass 65 75 65 75 90 90 80 20 85 80 75 85 85 90 80 75 70 75 20 60 80 45 80 95 75 75 70 80 75 85 Blackgrass 0 0 0 0 0 0 5 0 5 0 0 5 15 5 0 10 5 10 0 0 5 0 5 5 0 0 0 0 0 0 Bromegrass, Downy 0 0 20 0 5 0 5 45 5 0 40 0 10 20 40 0 5 0 0 0 0 0 0 0 5 5 5 0 0 0 Canarygrass 0 0 0 0 0 0 15 45 0 0 20 35 20 0 60 10 5 25 0 0 0 0 0 0 5 40 0 5 5 0 Chickweed 75 70 80 75 85 80 80 90 95 90 90 85 80 100 75 75 70 85 90 80 95 75 75 95 80 80 75 60 98 85 Cocklebur 65 75 0 20 40 0 95 0 5 85 75 95 85 98 90 10 75 20 25 70 45 70 75 95 98 95 40 90 98 75 Corn 0 0 20 0 0 0 5 5 5 0 0 50 10 20 15 80 15 25 20 0 0 0 45 20 35 40 0 — 65 15 Crabgrass, Large 65 75 80 80 95 55 80 75 85 70 85 90 85 85 95 85 65 80 80 70 70 45 75 75 75 85 55 70 75 60 Cupgrass, Woolly 10 45 60 10 10 20 10 65 65 55 70 75 75 50 75 35 45 70 10 45 — 45 70 55 65 70 — 70 65 40 Deadnettle — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — Foxtail, Giant 20 65 70 25 75 65 70 75 75 75 80 75 90 75 95 70 65 85 65 70 65 45 65 60 65 75 70 70 75 45 Foxtail, Green 60 10 70 20 65 40 60 90 5 60 90 80 70 75 95 60 65 70 75 50 10 20 50 40 30 50 20 80 70 5 Galium — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — Goosegrass 75 60 65 65 75 65 45 70 65 75 75 70 70 75 65 55 60 30 60 60 45 65 70 60 60 75 70 55 75 60 Johnsongrass 65 0 10 0 0 0 0 0 5 65 95 80 95 5 95 25 10 65 20 10 — 5 20 15 55 70 0 20 60 10 Kochia 0 75 75 75 75 75 75 0 75 10 65 75 75 100 75 65 65 20 75 65 — 80 65 65 65 80 — 65 98 70 Lambsquarters 75 90 85 95 98 95 95 95 95 80 95 98 100 98 95 95 85 85 90 85 80 80 90 90 95 98 95 95 90 98 Morningglory 65 20 0 60 20 75 80 85 75 65 70 95 70 45 90 70 65 75 80 70 55 100 65 100 70 100 60 65 100 75 Nutsedge, Yellow 10 35 20 20 10 45 25 10 65 10 10 75 65 10 25 35 60 50 45 45 20 75 70 75 50 45 — 45 75 50 Oat, Wild 0 0 55 20 0 0 40 20 25 0 10 5 20 50 50 10 0 30 0 0 0 0 0 0 10 10 0 5 0 0 Pigweed 85 80 80 90 100 98 100 100 98 75 80 100 98 98 98 80 85 100 90 90 100 85 90 95 100 100 90 70 95 95 Ragweed 75 75 75 75 80 75 80 50 75 75 75 80 80 85 75 70 60 85 40 65 40 75 80 85 70 65 70 70 75 80 Ryegrass, Italian 0 0 35 5 0 0 20 0 0 0 0 0 25 5 5 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 Soybean 65 80 80 75 80 25 75 75 85 75 75 80 80 98 75 90 98 75 90 55 65 95 65 70 90 98 95 75 95 45 Surinam Grass 50 75 80 20 50 65 20 45 75 65 75 75 80 75 95 55 65 85 25 50 — 45 75 65 65 70 — 60 75 55 Velvetleaf 75 98 95 98 100 90 95 85 100 85 85 90 98 100 80 90 85 98 95 85 — 85 95 100 95 95 — 98 90 100 Wheat 0 0 0 5 0 0 10 5 5 0 0 0 5 35 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 Windgrass 5 5 70 5 30 10 50 50 10 5 5 40 30 55 40 0 0 10 0 5 0 0 5 5 0 5 0 5 5 0 31 g ai/ha Compounds 109 111 113 117 118 119 120 121 122 123 126 127 128 129 130 131 140 141 146 147 152 155 156 157 159 160 Barley 0 0 0 0 0 0 — 0 0 5 5 0 0 0 0 0 0 0 0 0 10 30 30 5 20 5 Bermudagrass 70 95 80 75 75 75 80 95 75 80 75 95 75 80 75 65 60 80 85 75 95 85 80 75 95 65 Blackgrass 0 5 0 0 5 5 30 5 5 20 5 5 5 0 0 0 0 5 5 10 20 10 5 0 20 5 Bromegrass, Downy 0 0 5 5 0 10 20 25 5 0 5 5 30 5 10 0 0 0 0 0 30 5 10 40 50 0 Canarygrass 0 0 65 0 0 5 0 0 10 25 15 5 10 0 5 0 0 0 0 0 35 10 15 40 80 5 Chickweed 90 95 98 85 90 70 60 100 70 70 65 65 90 85 98 65 0 60 70 70 10 100 80 100 100 85 Cocklebur 75 98 95 75 40 0 10 40 20 65 15 75 98 95 85 95 0 40 10 50 70 15 20 100 95 98 Corn 0 10 25 10 0 20 15 25 0 35 10 5 40 20 55 0 0 0 0 0 25 5 10 70 60 15 Crabgrass, Large 65 70 85 75 70 75 80 85 75 70 75 80 85 80 85 75 50 70 65 60 75 60 45 80 80 80 Cupgrass, Woolly — 40 85 65 65 75 70 95 65 25 65 75 85 80 80 50 50 65 60 65 95 20 40 85 70 65 Deadnettle — — — — — — — — — — — — — — — — — — — — — — — — — — Foxtail, Giant 70 60 80 65 75 75 75 95 70 65 70 80 95 70 90 75 65 75 75 65 80 65 75 98 85 70 Foxtail, Green 20 40 80 50 50 85 90 80 80 50 50 75 85 80 90 70 45 50 50 40 75 25 45 70 85 55 Galium — — — — — — — — — — — — — — — — — — — — — — — — — — Goosegrass 65 70 70 45 55 75 75 95 40 65 65 65 90 85 85 65 45 65 75 35 80 65 65 85 85 80 Johnsongrass 5 10 65 5 10 10 15 20 45 35 65 65 70 40 60 5 10 15 45 15 70 10 15 70 45 45 Kochia 70 80 98 45 45 40 10 95 0 60 10 45 60 80 85 35 0 20 40 40 10 35 10 0 40 90 Lambsquarters 98 98 95 95 85 85 80 95 60 80 70 75 95 90 98 85 45 80 95 85 85 98 80 98 100 95 Morningglory 70 100 98 10 10 10 15 5 60 70 75 65 80 90 95 70 0 60 0 50 45 55 80 20 60 75 Nutsedge, Yellow — 65 65 0 35 10 5 5 55 65 65 65 20 35 10 15 10 0 5 50 65 20 45 30 40 65 Oat, Wild 0 0 20 5 5 50 50 60 5 0 5 5 40 0 20 0 0 10 0 5 30 10 5 30 60 10 Pigweed 100 95 95 95 85 95 95 100 85 80 75 80 95 85 95 90 55 60 95 85 95 98 60 65 95 90 Ragweed 75 75 80 70 70 70 50 65 60 70 55 70 85 90 85 80 25 65 65 20 60 45 65 90 90 80 Ryegrass, Italian 0 0 40 0 5 5 10 40 5 0 0 0 0 0 0 0 0 0 5 5 5 5 0 10 30 0 Soybean 95 70 98 65 75 0 40 90 45 60 70 95 98 95 98 75 10 70 70 15 70 95 80 95 95 85 Surinam Grass 65 60 85 65 50 75 20 95 75 25 70 75 50 80 80 20 50 40 65 50 75 40 40 75 75 40 Velvetleaf 90 80 85 70 75 75 75 98 80 80 80 90 90 95 95 80 50 75 80 60 85 100 60 100 100 90 Wheat 0 0 0 0 0 10 20 5 15 10 5 5 0 0 5 0 5 0 0 0 35 15 15 0 40 10 Windgrass 30 0 5 40 50 60 60 80 5 30 10 25 50 45 60 0 0 25 45 10 50 50 40 60 45 20 31 g ai/ha Compounds 162 164 169 173 181 184 186 187 189 190 191 193 197 217 218 219 220 225 226 227 228 229 233 235 236 237 Barley 30 5 0 5 5 5 0 0 0 0 5 0 0 0 30 0 10 20 10 0 0 0 0 0 0 5 Bermudagrass 85 70 70 98 100 98 80 75 10 98 100 95 95 70 70 95 80 80 80 75 80 75 95 98 95 98 Blackgrass 30 5 5 5 0 30 0 0 0 5 30 10 0 0 0 50 10 0 5 0 5 0 5 45 0 50 Bromegrass, Downy 20 40 10 5 40 40 5 5 0 5 35 10 15 10 5 45 10 35 0 0 5 5 40 10 0 30 Canarygrass 40 40 40 10 50 45 5 10 0 0 20 5 5 0 0 35 10 60 5 0 0 5 0 20 0 30 Chickweed 90 80 100 65 100 100 95 100 98 — 98 95 100 75 100 100 95 25 75 65 98 70 90 98 75 90 Cocklebur 100 98 100 60 100 100 90 100 60 40 90 95 80 80 — — — 98 98 75 98 85 90 — — — Corn 50 15 45 5 70 80 10 50 20 0 65 0 15 0 0 10 25 40 75 20 80 70 30 95 15 85 Crabgrass, Large 80 95 85 70 98 100 80 85 75 60 85 75 75 80 40 90 70 75 85 80 80 80 80 98 75 95 Cupgrass, Woolly 90 75 85 85 80 75 70 80 70 75 85 75 70 25 40 85 60 75 80 55 75 70 80 95 70 100 Deadnettle — — — — — 100 90 80 85 65 90 100 100 — — — — — — — — — — — — — Foxtail, Giant 85 90 95 95 98 98 75 98 75 70 100 75 85 70 40 70 30 75 85 75 85 75 90 98 75 98 Foxtail, Green 98 70 60 55 70 30 50 65 65 25 40 40 5 55 60 70 60 85 70 50 85 40 85 90 80 80 Galium — — — — — 50 40 20 20 50 20 75 75 — — — — — — — — — — — — — Goosegrass 60 85 95 80 95 100 85 85 60 70 95 85 85 80 0 90 80 85 80 75 80 70 85 95 80 95 Johnsongrass 98 45 60 65 100 100 65 90 50 60 70 50 70 0 — — 60 60 85 45 75 70 0 70 0 100 Kochia 20 98 100 65 65 0 75 40 85 0 5 20 65 75 35 80 45 5 80 70 90 55 70 98 80 65 Lambsquarters 80 98 100 98 100 80 98 98 98 80 75 98 95 90 98 100 100 85 90 90 98 85 98 98 98 95 Morningglory 75 90 95 75 95 40 95 80 100 40 40 40 98 70 70 60 65 95 98 100 100 98 65 95 60 85 Nutsedge, Yellow 25 40 0 45 60 35 65 45 20 35 40 60 45 10 10 10 10 10 55 10 40 0 0 45 0 20 Oat, Wild 35 25 0 50 65 40 0 10 5 0 50 0 40 30 40 50 10 45 25 0 0 0 30 35 0 40 Pigweed 100 98 100 85 100 70 85 100 80 65 80 90 80 85 100 100 95 90 75 80 98 80 85 100 85 80 Ragweed 90 85 100 55 98 — 85 95 10 — — — — 80 95 80 90 75 80 60 70 80 80 98 80 95 Ryegrass, Italian 40 5 0 0 10 20 0 0 0 0 40 5 0 0 30 20 5 0 0 0 0 0 30 30 0 50 Soybean 98 80 90 60 100 98 85 98 90 80 90 80 98 75 85 95 80 85 95 55 95 95 98 98 90 95 Surinam Grass 65 60 — — 70 80 — 65 65 60 70 65 50 70 75 10 50 75 75 55 75 65 80 80 60 85 Velvetleaf 80 70 100 100 100 85 70 90 85 100 75 90 80 98 85 85 80 80 85 80 80 75 80 95 98 85 Wheat 10 0 0 10 40 30 0 0 0 0 35 30 0 30 0 40 0 30 10 0 0 0 10 45 0 50 Windgrass 40 5 15 30 40 60 10 10 25 15 55 50 10 50 10 35 5 50 10 0 5 0 50 85 30 60 31 g ai/ha Compounds 238 239 240 243 244 245 255 Barley 10 0 5 60 50 45 30 Bermudagrass 95 95 98 98 80 80 90 Blackgrass 40 5 40 60 50 40 5 Bromegrass, Downy 10 0 10 50 40 60 50 Canarygrass 20 0 5 90 80 80 50 Chickweed 80 90 90 80 80 80 95 Cocklebur — 90 — — — — — Corn 80 5 90 90 85 100 60 Crabgrass, Large 95 75 80 95 80 80 85 Cupgrass, Woolly 95 75 98 95 100 100 85 Deadnettle — — — — — — — Foxtail, Giant 100 75 100 95 95 98 95 Foxtail, Green 85 80 90 98 85 85 85 Galium — — — — — — — Goosegrass 95 80 95 95 85 98 90 Johnsongrass 60 0 — 100 85 100 80 Kochia 90 90 80 85 85 85 10 Lambsquarters 100 98 98 100 100 98 90 Morningglory — 95 — 95 90 90 75 Nutsedge, Yellow 20 30 10 65 45 40 10 Oat, Wild 30 0 25 80 50 70 65 Pigweed 100 95 — 85 95 80 80 Ragweed 100 95 98 90 98 95 50 Ryegrass, Italian 20 0 10 60 35 40 10 Soybean 98 70 95 95 85 95 95 Surinam Grass 95 25 95 90 90 100 80 Velvetleaf 80 100 75 100 100 100 95 Wheat 40 0 30 85 60 75 35 Windgrass 45 20 60 80 50 65 50 16 g ai/ha 8 g ai/ha Compounds Compound 2 69 122 131 159 169 225 159 Barley 0 0 0 0 20 0 5 0 Bermudagrass 40 85 65 60 80 70 40 70 Blackgrass 0 0 0 0 5 0 0 0 Bromegrass, Downy 20 30 5 0 15 0 30 15 Canarygrass 20 0 0 0 40 5 55 25 Chickweed 70 95 65 45 100 90 15 80 Cocklebur 75 0 0 80 80 100 85 75 Corn 15 0 0 0 25 20 10 15 Crabgrass, Large 70 95 65 65 75 75 70 65 Cupgrass, Woolly 75 75 65 10 65 75 70 60 Foxtail, Giant 70 80 65 65 80 75 75 75 Foxtail, Green 50 75 40 40 80 45 85 50 Goosegrass 80 75 10 65 80 80 80 70 Johnsongrass 75 75 20 0 45 40 20 10 Kochia 55 60 0 20 20 100 5 20 Lambsquarters 80 100 55 75 95 95 85 90 Morningglory 55 65 55 5 10 95 80 0 Nutsedge, Yellow 40 5 35 0 20 0 5 10 Oat, Wild 5 50 5 0 35 0 25 0 Pigweed 70 95 75 60 75 90 80 55 Ragweed 65 75 55 65 80 98 70 65 Ryegrass, Italian 0 0 5 0 0 0 0 0 Soybean 75 45 20 75 85 55 65 80 Surinam Grass 70 75 25 15 65 — 35 65 Velvetleaf — 75 75 70 100 75 80 98 Wheat 0 0 5 0 35 0 20 10 Windgrass 10 40 5 0 40 5 5 10 Preemergence 250 g ai/ha Compounds 3 7 9 10 11 12 14 24 26 27 29 33 34 36 37 38 39 40 42 44 45 46 47 48 49 50 Bermudagrass 90 98 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 98 100 100 100 100 Blackgrass 0 0 40 20 60 10 0 10 10 30 50 30 50 25 10 40 0 5 5 60 5 0 5 5 0 5 Bromegrass, Downy 0 0 10 0 5 0 0 20 10 30 5 30 80 10 0 40 0 10 0 5 5 0 10 45 — 0 Cocklebur 100 75 100 98 100 100 95 95 98 90 90 90 85 80 45 90 45 100 — 45 — 15 — 85 55 — Corn 5 0 10 0 35 75 10 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass, Large 100 95 100 95 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 98 100 100 100 100 Cupgrass, Woolly 10 45 60 40 75 85 70 90 85 80 90 85 100 65 70 80 10 85 5 85 75 60 90 95 20 70 Foxtail, Giant 0 25 98 45 100 100 90 100 90 95 100 98 100 80 75 95 75 98 10 98 75 25 100 98 45 90 Foxtail, Green 0 0 — 30 65 80 60 100 70 80 100 100 100 85 90 100 100 100 85 100 100 10 98 98 30 100 Galium 50 0 95 85 75 95 80 80 98 95 100 90 98 95 100 85 85 90 50 98 85 70 95 70 95 98 Goosegrass 98 60 100 98 100 100 100 100 100 100 100 98 100 100 100 100 100 100 100 100 100 98 100 100 100 100 Johnsongrass 10 0 98 75 98 98 95 90 90 85 90 20 100 85 90 95 75 90 65 95 85 70 100 98 10 95 Kochia 100 100 100 100 100 100 100 100 100 100 100 — — — — — — — — — — — — — — — Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 98 100 Morningglory 100 20 98 40 100 100 100 100 100 100 100 90 98 20 0 100 100 65 0 95 0 0 55 100 85 55 Nightshade 100 100 100 100 100 100 100 100 100 100 100 100 100 98 85 100 100 100 100 100 100 98 100 100 98 100 Nutsedge, Yellow 50 55 95 75 90 90 85 90 85 90 85 90 90 75 90 80 10 85 85 90 70 90 90 90 90 90 Oat, Wild 0 0 60 10 40 5 0 80 5 50 50 50 60 0 10 20 0 30 0 30 5 0 10 15 0 0 Pigweed 95 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Ragweed 90 90 100 100 100 100 90 100 100 100 100 100 90 90 98 95 95 95 80 95 95 100 95 95 95 100 Russian Thistle — — — — — — — — — — — — — — — — — — — — — — — — — — Ryegrass, Italian 0 0 40 0 0 0 0 10 0 0 40 5 10 0 0 40 0 5 0 0 0 0 0 0 5 0 Soybean 50 30 80 75 95 95 85 85 90 90 95 75 80 40 35 75 0 70 0 0 0 25 0 20 85 0 Sunflower 85 25 98 98 98 100 98 98 95 100 100 90 90 85 90 75 65 80 75 80 75 60 85 80 75 85 Surinam Grass 5 10 95 80 75 100 80 100 90 95 95 100 90 100 100 80 15 90 75 100 98 90 100 100 85 100 Velvetleaf 100 100 100 100 100 100 100 100 100 95 100 100 100 100 98 100 98 100 90 100 95 65 100 100 100 100 Wheat 0 0 5 5 5 0 0 0 0 5 0 5 0 0 0 5 0 — 0 0 0 0 0 0 0 0 250 g ai/ha Compounds 51 52 53 55 56 58 59 61 62 63 64 66 67 68 72 73 74 75 77 81 113 119 120 193 217 218 Bermudagrass 100 100 100 100 100 100 98 98 100 98 98 98 100 100 100 100 100 100 100 100 100 100 100 98 100 100 Blackgrass 20 10 60 30 5 30 40 0 0 40 0 5 5 5 5 10 10 10 0 35 20 70 50 70 0 20 Bromegrass, Downy 40 5 30 0 5 0 0 0 0 0 0 0 0 5 0 20 0 0 0 0 10 55 85 50 0 0 Cocklebur 75 75 70 15 0 65 75 65 10 10 70 0 20 80 80 65 80 90 65 85 100 85 98 95 85 100 Corn 0 0 20 0 0 0 0 0 — 0 0 0 0 0 0 10 0 0 0 55 0 50 55 5 0 0 Crabgrass, Large 100 100 100 98 98 100 98 98 98 100 98 100 100 100 100 100 100 100 100 100 100 100 100 100 100 98 Cupgrass, Woolly 85 80 95 55 70 85 85 0 10 10 10 75 10 85 65 80 5 75 0 85 95 100 90 90 80 85 Foxtail, Giant 75 75 100 10 80 75 75 45 20 10 65 80 65 75 65 80 45 80 45 98 85 100 100 80 85 85 Foxtail, Green 100 100 98 0 100 100 98 75 10 30 50 75 40 85 90 80 0 98 15 100 100 100 100 98 90 100 Galium 95 95 90 85 85 80 98 98 0 20 70 0 90 85 85 85 98 98 90 100 95 100 98 100 90 100 Goosegrass 100 100 100 98 100 100 100 98 98 100 100 98 98 98 100 100 100 100 98 100 100 100 100 100 100 98 Johnsongrass 80 95 75 0 80 85 90 20 — 60 75 98 0 95 10 98 0 70 0 90 70 95 90 60 55 45 Kochia — — — — — — 98 — 100 100 95 85 85 95 85 90 85 95 95 70 90 98 75 90 — — Lambsquarters 98 100 100 100 98 98 100 — 100 100 98 100 98 100 100 100 100 100 100 98 100 100 100 100 100 100 Morningglory 70 55 65 65 65 75 60 65 20 55 0 80 80 85 75 70 80 90 90 95 — 95 100 95 0 65 Nightshade 100 100 100 100 100 100 100 — 98 98 98 98 98 100 100 100 100 100 100 100 100 100 98 100 100 100 Nutsedge, Yellow 90 90 90 65 90 90 90 90 — 90 10 95 75 90 90 85 90 90 90 95 90 98 98 90 90 90 Oat, Wild 0 60 70 0 0 30 0 0 0 0 5 40 0 5 0 65 5 0 0 0 40 80 65 60 0 0 Pigweed 100 100 100 100 100 100 100 — 100 100 98 98 98 100 100 100 100 100 100 100 100 100 100 100 100 100 Ragweed 90 95 90 90 80 90 95 90 60 85 85 55 50 90 85 85 100 95 95 90 98 95 95 100 95 100 Russian Thistle — — — — — — — — — — — — 90 98 80 — 98 — — 100 — 100 — 100 — — Ryegrass, Italian 5 0 50 0 0 0 20 5 20 0 0 5 0 0 0 5 0 0 0 0 40 100 100 45 10 5 Soybean 85 80 85 65 90 95 80 20 — 15 — — — — — — — — — — 90 80 80 80 0 90 Sunflower 75 75 65 70 75 75 80 70 55 70 55 10 55 85 80 75 85 85 85 90 95 85 95 95 85 95 Surinam Grass 100 98 100 45 98 95 95 35 60 85 90 100 75 85 98 100 95 75 100 100 98 100 100 45 90 100 Velvetleaf 100 100 100 100 98 95 100 100 95 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Wheat 10 0 10 0 10 0 0 0 0 0 0 0 0 0 0 30 0 0 0 0 10 50 30 25 0 0 250 g ai/ha 125 g ai/ha Compounds Compounds 219 220 243 244 245 255 2 3 7 9 10 11 12 14 24 26 27 29 33 34 36 37 38 39 40 42 Bermudagrass 100 100 100 100 100 100 100 80 85 100 100 100 100 100 100 98 100 100 100 100 100 98 100 100 100 100 Blackgrass 60 35 95 70 45 60 50 0 0 20 0 30 5 0 0 0 10 50 10 50 25 5 30 0 0 0 Bromegrass, Downy 20 5 70 30 15 40 5 0 0 5 0 0 0 0 0 0 0 0 5 10 0 0 5 0 5 0 Cocklebur 85 0 98 100 100 — 80 70 0 65 65 95 98 85 95 85 85 90 85 75 — 0 25 — 85 — Corn 0 0 95 85 65 0 0 0 0 0 0 0 15 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass, Large 100 100 100 100 100 100 100 85 45 100 70 100 100 100 100 100 100 100 100 100 100 10 100 100 100 95 Cupgrass, Woolly 80 25 100 100 100 90 20 0 0 45 35 15 75 50 85 50 60 55 60 100 10 10 60 0 70 0 Foxtail, Giant 80 75 95 100 100 98 70 0 0 60 0 75 70 75 90 45 85 100 95 90 65 0 80 70 80 10 Foxtail, Green 100 100 100 90 100 100 60 0 0 5 0 65 40 10 100 30 50 100 100 90 85 0 85 75 85 85 Galium 100 100 100 98 95 100 — 30 0 60 85 50 90 40 10 90 85 98 50 90 80 30 85 85 85 10 Goosegrass 100 100 100 100 100 100 100 85 45 100 95 100 100 98 100 95 100 100 90 100 95 80 100 100 100 100 Johnsongrass 80 80 100 100 100 98 80 0 0 90 60 85 75 80 90 60 50 30 0 98 80 45 85 65 85 10 Kochia — — 100 100 100 — 100 100 100 100 100 100 100 100 100 100 100 100 — — — — — — — — Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Morningglory 100 90 100 100 100 90 75 100 0 70 0 35 85 100 100 100 100 100 70 75 0 0 0 15 0 0 Nightshade 100 100 98 100 100 100 100 98 95 100 100 100 100 100 100 100 100 100 100 100 95 80 98 100 98 100 Nutsedge, Yellow 90 90 95 95 80 90 70 40 15 80 55 85 75 40 85 50 30 60 70 75 40 20 70 0 65 75 Oat, Wild 40 60 90 40 30 90 50 0 0 0 0 10 0 0 0 0 30 45 30 30 0 0 0 0 0 0 Pigweed 100 100 100 100 100 100 100 90 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Ragweed 98 95 98 100 100 100 98 90 15 100 100 100 100 90 98 95 100 100 100 90 85 65 80 75 90 25 Russian Thistle — — 100 — — — — — — — — — — — — — — — — — — — — — — — Ryegrass, Italian 10 0 70 45 40 30 5 0 0 0 0 0 0 0 10 0 0 10 5 5 0 0 5 0 5 0 Soybean 75 75 95 95 75 80 70 35 20 — 65 65 80 50 80 80 80 90 65 65 0 0 0 0 20 0 Sunflower 85 90 95 100 95 90 90 70 0 95 95 95 98 85 95 90 90 90 75 80 55 45 25 25 75 55 Surinam Grass 100 65 100 100 100 100 60 0 0 95 15 35 95 60 95 90 60 90 95 65 100 55 65 10 85 10 Velvetleaf 95 100 100 100 100 100 100 90 100 100 100 100 100 100 100 100 90 100 100 95 100 20 98 75 100 85 Wheat 0 5 70 45 15 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 125 g ai/ha Compounds 44 45 46 47 48 49 50 51 52 53 55 56 58 59 61 62 63 64 66 67 68 69 72 73 74 75 77 Bermudagrass 100 100 — 100 100 98 100 100 98 100 100 100 100 98 75 95 98 98 98 95 98 100 98 98 100 100 100 Blackgrass 40 0 0 5 0 0 0 10 0 5 0 0 5 30 0 0 5 0 5 0 0 0 0 0 0 5 0 Bromegrass, Downy 0 0 0 5 0 0 0 5 5 5 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 Cocklebur — — 0 — 0 45 75 20 10 65 10 0 10 10 20 0 0 10 0 15 — 10 70 60 70 75 10 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass, Large 100 100 85 100 100 98 100 100 100 100 95 98 98 98 98 80 100 98 95 98 98 100 100 100 100 100 98 Cupgrass, Woolly 80 60 50 75 75 0 15 75 65 85 0 50 20 65 0 5 0 0 60 0 55 45 45 55 0 55 0 Foxtail, Giant 75 45 15 85 85 20 90 50 25 100 0 75 75 60 15 20 0 35 75 45 55 90 10 75 5 80 5 Foxtail, Green 98 80 5 98 98 5 95 98 45 98 0 20 70 90 40 10 — 0 30 — 25 85 50 30 0 50 0 Galium 65 50 0 50 60 90 95 80 70 0 20 60 30 95 98 0 0 30 0 85 70 0 85 80 40 95 85 Goosegrass 100 100 98 100 100 98 100 100 100 100 98 95 100 100 98 98 100 98 90 90 98 100 100 100 100 100 98 Johnsongrass 90 75 45 80 90 0 90 75 90 60 0 55 80 80 10 0 55 55 85 0 75 85 0 98 0 65 0 Kochia — — — — — — — — — — — — — 60 85 100 100 45 85 80 95 45 85 80 85 90 90 Lambsquarters 100 100 95 100 100 98 100 98 100 100 98 98 98 100 98 100 100 98 98 98 98 100 98 100 98 100 100 Morningglory 50 — 0 0 100 80 — 20 45 25 45 45 55 55 45 0 0 0 25 15 65 0 65 45 75 75 75 Nightshade 100 100 98 100 100 98 100 98 98 100 100 98 98 100 98 98 98 95 98 95 100 98 98 98 98 98 98 Nutsedge, Yellow 75 20 80 80 85 85 90 85 80 90 45 85 75 85 90 45 25 0 85 65 85 0 75 65 65 90 90 Oat, Wild 5 0 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 Pigweed 100 100 95 100 100 100 100 100 100 100 98 100 100 100 100 100 100 85 98 98 100 100 100 100 100 100 100 Ragweed 95 80 100 90 90 80 95 80 85 85 85 70 85 90 75 45 70 75 45 35 80 65 80 75 98 95 90 Russian Thistle — — — — — — — — — — — — — — — — — — — — 80 100 80 — 90 — — Ryegrass, Italian 0 0 0 0 0 0 0 0 0 0 0 0 0 20 5 0 0 0 0 0 0 0 0 0 0 0 0 Soybean 0 0 15 0 0 85 — 80 55 80 15 80 85 0 0 80 5 — — — — — — — — — — Sunflower 75 10 0 80 80 75 85 75 70 65 60 65 65 70 60 10 20 0 0 35 75 5 65 70 70 75 75 Surinam Grass 90 98 75 100 100 75 98 98 95 100 0 98 85 85 0 25 55 85 90 15 55 100 75 100 85 60 75 Velvetleaf 100 85 55 90 100 100 100 98 98 98 100 98 95 100 98 95 100 95 95 90 100 85 100 100 100 100 100 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 125 g ai/ha 62 g ai/ha Compounds Compounds 81 113 119 120 193 217 218 219 220 243 244 245 255 2 3 7 9 10 11 12 14 24 26 27 29 33 Bermudagrass 100 100 100 100 95 100 100 100 98 100 100 100 100 100 70 0 100 80 100 100 75 100 70 98 100 100 Blackgrass 35 0 50 50 30 0 0 40 20 70 60 30 40 0 0 0 0 0 5 0 0 0 0 0 5 0 Bromegrass, Downy 0 10 55 30 5 0 0 10 0 60 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Cocklebur 75 90 70 60 — 85 90 — — 95 100 98 — 65 10 0 25 15 75 80 85 — 40 85 80 80 Corn 50 0 50 25 5 0 0 0 0 85 60 25 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass, Large 100 100 100 100 100 100 65 100 80 100 100 100 100 100 70 0 90 0 100 90 50 98 40 80 100 98 Cupgrass, Woolly 75 85 95 75 80 65 65 20 10 95 95 80 75 15 0 0 15 10 0 10 5 70 5 0 10 50 Foxtail, Giant 85 60 95 98 70 75 20 10 0 95 100 90 55 20 0 0 15 0 35 20 10 85 10 5 50 45 Foxtail, Green 100 60 100 100 50 0 80 90 — 100 90 75 80 5 0 0 0 0 25 0 0 40 0 30 40 45 Galium 100 85 90 95 100 70 95 98 90 98 98 95 60 — 5 0 40 10 50 50 0 0 50 50 80 10 Goosegrass 100 100 100 100 100 100 98 100 98 100 100 100 100 100 70 25 98 75 95 95 85 98 80 98 100 85 Johnsongrass 90 60 95 80 15 20 20 65 0 95 100 80 75 65 0 0 85 10 55 0 30 85 10 5 5 0 Kochia 65 85 55 50 80 — — — — 90 95 98 — 100 — 100 100 50 100 100 100 100 100 100 100 — Lambsquarters 98 100 100 100 100 100 100 100 100 100 100 100 100 100 — 100 100 100 100 100 100 100 100 100 100 100 Morningglory 80 — 95 90 95 0 15 15 0 98 98 65 65 20 100 0 40 0 0 55 100 100 100 100 100 15 Nightshade 98 100 98 95 100 100 100 100 98 98 100 100 100 100 — 90 100 100 100 100 98 98 100 98 90 100 Nutsedge, Yellow 95 90 98 98 70 70 90 85 60 90 80 65 40 40 10 10 45 0 55 60 30 50 50 20 30 45 Oat, Wild 0 20 50 65 30 0 0 5 0 85 10 30 60 5 0 0 0 0 0 0 0 0 0 0 0 0 Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100 — 100 100 100 100 100 98 100 100 100 100 100 Ragweed 90 95 95 95 100 90 98 85 80 98 100 100 85 85 65 0 90 100 100 98 90 90 85 85 90 85 Russian Thistle 100 — 100 80 100 — — — — 100 — — — — — — — — — — — — — — — — Ryegrass, Italian 0 5 100 100 25 5 5 5 0 45 5 0 10 0 0 0 0 0 0 0 0 0 0 0 0 0 Soybean — 85 80 80 60 0 80 65 0 85 90 55 15 60 30 0 10 60 45 65 — 60 60 70 85 60 Sunflower 85 90 70 85 80 85 90 80 70 95 85 80 75 70 70 0 85 80 85 98 85 90 90 75 85 75 Surinam Grass 100 95 100 100 30 85 98 45 45 100 100 100 95 20 0 0 45 10 25 60 5 75 5 20 20 65 Velvetleaf 100 100 100 100 100 100 90 90 90 100 100 100 98 90 90 85 100 100 100 100 98 100 90 85 90 90 Wheat 0 10 30 25 10 0 0 0 0 70 5 5 0 0 0 0 0 — 0 0 0 0 0 0 0 0 62 g ai/ha Compounds 34 36 37 38 39 40 42 44 45 46 47 48 49 50 51 52 53 55 56 58 59 61 62 63 64 66 67 Bermudagrass 100 100 80 100 100 100 100 100 100 — 100 100 — 100 98 98 100 98 100 98 98 75 75 98 85 80 90 Blackgrass 5 25 0 5 0 0 0 30 0 0 5 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 Bromegrass, Downy 0 0 0 0 0 0 0 0 0 0 5 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 Cocklebur 55 — — 10 — — 0 — — 0 0 0 20 75 0 0 20 10 0 0 0 10 0 0 0 0 0 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 — 0 0 0 0 Crabgrass, Large 100 90 0 90 95 98 85 75 95 75 95 90 95 100 98 98 100 60 85 98 95 85 50 85 75 85 65 Cupgrass, Woolly 100 0 0 10 0 50 0 45 45 45 45 10 0 5 35 10 55 0 20 10 65 0 0 0 0 40 0 Foxtail, Giant 55 20 0 40 45 65 0 45 0 0 70 75 0 75 45 15 85 0 40 20 0 0 0 0 25 20 0 Foxtail, Green 70 80 0 30 — 85 65 98 80 0 80 60 0 50 50 30 60 0 20 5 70 0 0 — 0 5 30 Galium 50 80 10 40 80 70 0 65 40 0 50 60 80 95 75 0 0 0 0 0 90 70 0 0 0 0 35 Goosegrass 100 90 0 100 100 98 95 98 100 95 100 100 95 98 100 100 100 95 95 98 98 98 95 98 40 75 85 Johnsongrass 75 65 0 80 60 80 0 75 45 10 75 45 0 20 5 75 55 0 45 20 — 0 0 0 0 55 0 Kochia — — — — — — — — — — — — — — — — — — — — 45 70 100 100 0 80 70 Lambsquarters 100 100 98 98 100 100 100 100 100 90 100 100 95 100 98 100 100 98 98 98 100 98 98 98 98 98 98 Morningglory 0 0 0 0 0 0 0 0 — 0 — 100 80 0 20 0 20 0 0 0 0 0 0 0 0 20 15 Nightshade 95 95 40 95 100 98 100 98 100 95 100 100 98 100 98 95 98 98 98 98 98 95 95 95 85 95 95 Nutsedge, Yellow 45 0 0 60 0 45 35 60 10 55 45 20 60 85 70 25 80 45 80 75 65 70 25 15 0 30 65 Oat, Wild 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 Pigweed 100 100 100 100 100 100 100 98 95 85 100 100 100 100 100 100 98 95 100 98 100 100 98 98 75 98 98 Ragweed 80 75 10 70 45 75 20 90 80 100 80 85 75 95 70 80 75 65 65 75 90 75 20 65 50 0 25 Russian Thistle — — — — — — — — — — — — — — — — — — — — — — — — 0 0 — Ryegrass, Italian 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Soybean 45 0 0 0 0 0 0 0 0 0 0 0 80 0 0 0 70 0 — — 0 0 80 0 — — — Sunflower 70 0 0 0 5 55 0 70 0 0 65 75 75 75 70 10 55 60 60 55 65 45 10 15 0 0 20 Surinam Grass 60 95 45 60 10 75 5 85 60 5 98 90 — 95 98 25 85 0 95 65 75 0 20 0 85 80 10 Velvetleaf 85 85 0 60 45 85 80 90 65 45 90 95 100 85 85 98 98 98 90 80 90 85 75 90 75 80 85 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 62 g ai/ha 31 g ai/ha Compounds Compounds 68 69 72 73 74 75 77 81 113 119 120 193 217 218 219 220 243 244 245 255 2 3 7 9 10 11 Bermudagrass 98 100 98 98 98 100 100 100 95 100 100 95 100 100 100 98 100 100 100 100 98 10 0 98 45 98 Blackgrass 0 0 0 0 0 0 0 0 0 30 50 0 0 0 35 20 10 35 5 20 0 0 0 0 0 0 Bromegrass, Downy 0 0 0 5 0 0 0 0 10 50 30 5 0 0 0 0 40 0 0 0 0 0 0 0 0 0 Cocklebur 10 0 50 0 45 20 0 10 75 — 35 75 — 0 75 0 75 90 0 — 0 10 0 0 0 35 Corn 0 0 0 0 0 0 0 40 0 40 — 0 0 0 0 0 75 25 5 0 0 0 0 0 0 0 Crabgrass, Large 95 100 100 98 98 100 98 100 98 100 100 100 100 20 98 75 100 100 100 95 15 0 0 0 0 60 Cupgrass, Woolly 20 0 0 20 0 — 0 55 50 75 70 70 5 0 10 0 95 55 70 10 0 0 0 0 0 0 Foxtail, Giant 20 75 5 70 0 25 0 75 40 85 98 65 40 0 0 0 85 80 10 45 15 0 0 0 0 0 Foxtail, Green 5 70 0 30 0 50 0 90 40 100 98 50 0 30 70 90 100 45 0 80 0 0 0 0 0 0 Galium 70 — 85 30 30 85 20 100 70 85 90 100 10 80 85 50 90 65 60 50 — 0 0 0 0 5 Goosegrass 95 100 98 98 98 100 95 98 90 100 100 100 98 60 100 95 100 100 100 98 85 30 10 75 0 70 Johnsongrass 5 45 0 0 0 10 0 80 5 85 70 0 5 0 15 0 95 85 75 60 60 0 0 0 0 0 Kochia 80 20 75 — — 90 90 55 80 0 20 70 — — — — 20 90 45 — 100 98 15 15 0 15 Lambsquarters 98 100 98 98 98 100 98 98 100 98 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Morningglory 55 0 55 0 60 60 65 65 — 95 90 90 0 0 0 0 — 90 0 55 0 100 — 0 0 0 Nightshade 98 98 95 95 98 98 98 98 98 98 95 100 100 98 98 90 98 100 100 90 98 50 80 100 100 85 Nutsedge, Yellow 70 0 70 65 55 80 80 75 80 95 90 65 65 75 45 0 80 60 0 25 15 5 0 0 0 0 Oat, Wild 0 0 0 0 0 0 0 0 5 45 10 5 0 0 0 0 85 5 0 0 — 0 0 0 0 0 Pigweed 98 100 98 100 98 100 100 100 98 90 100 100 100 100 100 100 98 100 95 100 100 85 100 50 100 100 Ragweed 75 65 70 60 98 75 75 85 90 80 80 100 60 95 75 60 95 95 85 75 60 65 0 55 98 65 Russian Thistle — 100 30 — 80 — — 100 — 100 80 98 — — — — 100 — — — — — — — — — Ryegrass, Italian 0 0 0 0 0 0 0 0 5 100 100 0 0 0 0 0 10 0 0 0 0 0 0 0 0 0 Soybean — — — — — — — — 65 55 70 60 0 65 0 0 75 80 10 0 15 0 0 0 10 25 Sunflower 60 0 25 20 55 55 75 75 80 60 — 80 75 80 45 45 85 80 70 60 50 50 0 45 0 75 Surinam Grass 50 100 75 100 80 60 20 100 80 98 100 15 75 65 10 20 98 100 100 85 15 0 0 0 0 0 Velvetleaf 100 70 100 100 100 100 100 100 100 80 100 100 100 85 75 70 100 100 100 95 75 50 40 98 55 100 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 40 0 0 0 0 0 0 0 0 0 31 g ai/ha Compounds 12 14 24 26 27 29 33 34 36 37 38 39 40 42 44 45 46 47 48 49 50 51 52 53 55 56 58 59 Bermudagrass 100 70 95 5 70 98 98 100 95 10 98 85 98 90 100 98 0 100 100 — 100 95 98 — 95 98 98 10 Blackgrass 0 0 0 0 0 5 0 0 20 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 Bromegrass, Downy 0 0 0 0 0 0 0 — 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Cocklebur 25 0 10 10 0 5 25 0 — 0 0 0 65 0 — — 0 — — 0 — 0 0 10 0 0 0 0 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass, Large 0 5 90 0 5 98 85 55 20 0 60 55 70 45 65 45 45 75 75 75 98 75 60 75 10 80 95 55 Cupgrass, Woolly 0 0 5 0 0 5 10 100 0 0 0 0 0 0 0 45 10 0 10 0 0 10 0 0 0 0 10 10 Foxtail, Giant 0 0 30 5 0 10 10 15 10 0 0 0 10 0 20 0 0 45 20 0 45 0 0 5 0 0 10 0 Foxtail, Green 0 0 0 0 0 0 0 50 35 0 20 — 0 65 0 0 0 65 60 0 50 50 0 60 0 0 0 — Galium 0 0 0 0 0 50 0 10 10 0 0 70 50 0 0 40 0 50 0 0 70 0 0 0 0 0 0 0 Goosegrass 85 70 85 5 80 95 80 95 0 0 95 85 80 50 90 80 85 95 98 20 95 98 98 98 45 90 95 98 Johnsongrass 0 5 20 0 0 0 0 20 0 0 10 0 10 0 10 0 0 65 20 0 0 0 10 10 0 10 10 — Kochia 15 85 100 80 100 98 — — — — — — — — — — — — — — — — — — — — — 0 Lambsquarters 100 100 98 98 100 100 98 100 98 95 98 100 100 100 100 100 90 100 100 95 100 95 98 98 95 95 85 98 Morningglory 40 100 100 100 100 100 0 0 0 0 0 0 0 0 0 0 0 0 0 45 0 0 0 0 0 0 0 — Nightshade 100 85 90 85 80 90 80 55 80 0 90 50 65 100 95 98 95 100 100 98 100 98 90 98 60 85 90 95 Nutsedge, Yellow 25 0 30 10 0 0 0 10 0 0 10 0 10 10 45 0 25 45 20 60 80 55 0 65 0 20 20 55 Oat, Wild 0 0 0 0 0 0 0 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Pigweed 100 90 98 98 100 100 100 100 100 100 100 90 98 100 98 85 85 98 100 100 90 100 90 95 45 98 85 90 Ragweed 90 70 85 65 85 80 80 75 35 0 40 0 75 0 20 45 100 45 65 70 75 65 80 65 55 20 20 75 Russian Thistle — — — — — — — — — — — — — — — — — — — — — — — — — — — — Ryegrass, Italian 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Soybean 60 25 45 50 70 20 60 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 10 — Sunflower 95 50 85 60 75 75 65 55 0 0 0 0 20 0 10 0 0 65 0 60 55 20 10 15 10 0 0 55 Surinam Grass 35 0 65 0 0 0 0 5 70 0 40 0 40 0 65 45 0 85 80 0 75 95 10 75 0 55 40 5 Velvetleaf 90 70 98 50 55 10 80 75 65 0 55 15 80 75 75 0 0 80 75 95 85 75 80 80 75 85 75 75 Wheat 0 0 0 0 0 0 0 — 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 31 g ai/ha Compounds 61 62 63 64 66 67 68 69 72 73 74 75 77 81 113 119 120 193 217 218 219 220 243 244 245 255 Bermudagrass 20 20 75 50 20 45 95 98 95 50 — 98 55 100 95 100 100 75 98 98 98 80 100 100 98 100 Blackgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 30 5 0 0 0 30 10 0 35 0 0 Bromegrass, Downy 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 0 0 0 0 Cocklebur 0 0 0 0 0 0 0 0 10 0 10 10 0 0 45 0 0 — — — — 0 — — 0 — Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 40 0 0 0 0 0 0 0 0 65 5 0 0 Crabgrass, Large 70 0 50 50 70 40 65 98 95 85 98 98 70 100 70 100 98 100 95 0 10 0 100 98 60 80 Cupgrass, Woolly 0 0 0 0 25 0 5 0 0 10 0 5 0 40 5 65 50 10 0 0 0 0 75 45 50 0 Foxtail, Giant 0 0 0 20 15 0 0 5 0 0 0 0 0 60 5 55 75 0 5 0 0 0 55 60 0 15 Foxtail, Green 0 0 0 0 0 0 0 — 0 0 0 5 0 80 10 95 95 5 0 0 20 80 35 0 0 0 Galium 70 0 0 0 0 0 0 — 0 — 20 60 0 85 50 65 80 75 0 60 75 0 85 55 20 0 Goosegrass 80 15 90 30 35 85 80 95 60 85 98 95 55 98 75 100 100 98 95 10 98 65 98 98 95 80 Johnsongrass 0 0 0 0 0 0 0 5 0 0 0 0 0 10 0 50 35 0 0 0 0 0 70 70 65 0 Kochia 0 98 0 0 80 70 80 0 45 0 80 80 85 45 80 0 0 20 — — — — 15 85 0 — Lambsquarters 90 98 98 95 98 98 98 98 98 95 98 98 98 98 98 95 100 100 95 100 100 100 100 100 100 98 Morningglory 0 0 0 0 0 0 0 0 0 0 10 0 0 — — 60 0 75 0 0 0 0 — 85 0 40 Nightshade 90 10 80 55 80 70 98 95 95 75 85 95 98 98 98 90 90 100 95 98 90 65 90 98 98 75 Nutsedge, Yellow 25 15 10 0 10 0 0 0 40 20 20 60 75 10 65 75 70 10 60 45 0 0 65 20 0 10 Oat, Wild 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 — 30 0 0 0 Pigweed 0 45 95 55 98 98 95 98 98 95 98 98 100 100 98 80 95 98 95 100 100 100 75 100 80 100 Ragweed 50 0 65 0 0 25 10 65 55 45 10 75 50 60 55 80 80 100 60 85 45 15 85 70 75 65 Russian Thistle — — — — — 85 — 100 0 0 0 — — 100 — 100 — 90 — — — — 100 — — — Ryegrass, Italian — 0 0 0 0 0 0 0 0 0 0 0 0 0 0 100 100 0 0 0 0 0 0 0 0 0 Soybean — 0 0 — — — — — — — — — — — 0 10 15 40 0 0 0 — 65 70 0 0 Sunflower 0 0 5 0 0 0 0 0 25 0 0 30 60 60 75 40 45 70 70 75 0 0 80 80 45 45 Surinam Grass 0 5 0 0 35 0 45 80 45 85 0 40 0 98 0 90 100 0 45 10 10 10 80 75 95 65 Velvetleaf 80 75 75 65 80 75 95 70 98 100 98 100 95 100 80 75 80 85 95 80 0 45 100 100 95 80 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 16 g ai/ha Compounds 2 69 Bermudagrass 25 90 Blackgrass 0 0 Bromegrass, Downy 0 0 Cocklebur 0 0 Corn 0 0 Crabgrass, Large 0 75 Cupgrass, Woolly 0 0 Foxtail, Giant 0 0 Foxtail, Green 0 — Goosegrass 0 55 Johnsongrass 0 0 Kochia 0 — Lambsquarters 100 95 Morningglory 0 0 Nightshade 55 80 Nutsedge, Yellow 0 0 Oat, Wild 0 0 Pigweed 98 95 Ragweed 25 40 Russian Thistle — 100 Ryegrass, Italian 0 — Soybean 0 — Sunflower 0 0 Surinam Grass 0 75 Velvetleaf 0 0 Wheat 0 0

Test C

Seeds of plant species selected from bluegrass (annual bluegrass, Poa annua), blackgrass (Alopecurus myosuroides), canarygrass (Phalaris minor), chickweed (common chickweed, Stellaria media), galium (catchweed bedstraw, Galium aparine), bromegrass (downy bromegrass, Bromus tectorum), field poppy (Papaver rhoeas), field violet (Viola arvensis), green foxtail (Setaria viridis), deadnettle (henbit deadnettle, Lamium amplexicaule), Italian ryegrass (Lolium multiflorum), kochia (Kochia scoparia), lambsquarters (Chenopodium album), oilseed rape (Brassica napus), pigweed (Amaranthus retroflexus), Russian thistle (Salsola iberica), spring barley (Hordeum vulgare), spring wheat (Triticum aestivum), buckwheat (wild buckwheat, Polygonum convolvulus), wild mustard (Sinapis arvensis), wild oat (Avena fatua), wild radish (Raphanus raphanistrum), windgrass (Apera spica-venti), winter barley (Hordeum vulgare), and winter wheat (Triticum aestivum) were planted and treated postemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage).

Treated plants and controls were maintained in a controlled growth environment for 14 days after which time all test plants were visually evaluated and compared to controls. Plant response ratings, summarized in Table C, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.

TABLE C 125 g ai/ha Postemergence Compounds 2 4 8 11 12 33 Barley, Spring 0 15 30 30 0 0 Barley, Winter 30 35 40 60 0 5 Blackgrass 30 40 35 35 40 35 Bluegrass 65 50 75 80 40 40 Bromegrass, Downy 50 40 40 65 20 20 Buckwheat, Wild 70 100 65 80 50 75 Canarygrass — 90 10 10 — 5 Chickweed — 100 98 100 — 100 Deadnettle 100 100 100 100 100 100 Field Poppy — 50 60 70 — 98 Field Violet 50 60 65 35 40 95 Foxtail, Green 95 95 98 95 90 95 Galium 70 90 90 65 80 60 Kochia 98 95 90 98 75 70 Lambsquarters 98 100 100 100 95 100 Mustard, Wild — 100 98 100 95 100 Oat, Wild 25 50 30 70 15 10 Oilseed Rape 90 100 100 100 95 100 Pigweed 90 100 98 98 75 98 Radish, Wild 95 95 100 95 90 98 Russian Thistle 95 95 95 95 70 90 Ryegrass, Italian 30 15 35 30 0 10 Wheat, Spring 0 20 20 40 0 10 Wheat, Winter 30 20 30 35 10 5 Windgrass 40 95 60 95 50 40 62 g ai/ha Postemergence Compounds 2 8 11 12 33 Barley, Spring 0 20 20 0 0 Barley, Winter 10 20 40 0 0 Blackgrass 20 35 35 30 35 Bluegrass 25 50 65 30 15 Bromegrass, Downy 30 35 65 15 15 Buckwheat, Wild 40 65 80 50 75 Canarygrass — 10 10 — 5 Chickweed — 95 98 — 98 Deadnettle 100 98 100 100 98 Field Poppy — 40 40 — 90 Field Violet 40 65 35 40 95 Foxtail, Green 95 95 95 80 95 Galium 50 90 65 60 50 Kochia 75 85 95 35 60 Lambsquarters 80 98 98 80 100 Mustard, Wild 98 98 98 95 98 Oat, Wild 25 30 50 15 5 Oilseed Rape 70 98 98 80 100 Pigweed 75 98 95 75 95 Radish, Wild 95 98 95 90 95 Russian Thistle 70 95 95 60 90 Ryegrass, Italian 15 20 30 0 10 Wheat, Spring 0 5 35 0 10 Wheat, Winter 0 25 30 0 5 Windgrass 25 20 85 — 25 31 g ai/ha Postemergence Compounds 2 4 8 11 12 33 Barley, Spring 0 10 10 15 0 0 Barley, Winter 0 5 20 20 0 0 Blackgrass 0 20 30 20 20 5 Bluegrass 25 35 25 35 20 0 Bromegrass, Downy 20 35 25 50 10 10 Buckwheat, Wild 20 95 65 70 15 65 Canarygrass — 0 5 5 — 0 Chickweed — 98 95 95 — 90 Deadnettle 95 98 95 98 100 98 Field Poppy — 30 20 30 — 80 Field Violet 40 40 65 0 35 90 Foxtail, Green 75 70 95 95 60 95 Galium 30 65 75 30 50 40 Kochia 70 90 70 90 10 50 Lambsquarters 75 100 98 98 80 98 Mustard, Wild 98 98 95 98 95 98 Oat, Wild 15 20 20 25 15 0 Oilseed Rape 60 90 90 95 70 98 Pigweed 40 95 95 95 65 95 Radish, Wild 80 80 95 95 80 95 Russian Thistle 60 70 90 80 60 80 Ryegrass, Italian 0 10 0 5 0 0 Wheat, Spring 0 15 5 20 0 10 Wheat, Winter 0 0 10 30 0 0 Windgrass 20 35 10 70 20 20 16 g ai/ha Postemergence Compounds 2 8 11 12 33 Barley, Spring 0 0 0 0 0 Barley, Winter 0 0 0 0 0 Blackgrass 0 20 20 0 0 Bluegrass 0 5 — 10 0 Bromegrass, Downy 10 10 30 0 0 Buckwheat, Wild 15 65 65 10 60 Canarygrass — 0 5 — 0 Chickweed — 95 95 — 90 Deadnettle 95 85 95 100 95 Field Poppy — 0 20 — 80 Field Violet 0 10 0 35 65 Foxtail, Green 65 95 95 50 80 Galium 5 50 20 5 35 Kochia 65 65 70 0 35 Lambsquarters 70 98 98 70 98 Mustard, Wild 98 — 98 80 98 Oat, Wild 0 20 25 0 0 Oilseed Rape 60 80 90 50 90 Pigweed 35 95 75 65 75 Radish, Wild 65 85 95 60 90 Russian Thistle 35 90 80 60 80 Ryegrass, Italian 0 0 0 0 0 Wheat, Spring 0 5 5 0 10 Wheat, Winter 0 10 0 0 0 Windgrass 5 0 60 5 0 Compounds 2 12 125 g ai/ha Preemergence Barley, Spring 0 0 Barley, Winter 0 0 Blackgrass 0 0 Bluegrass 0 35 Bromegrass, Downy 0 0 Buckwheat, Wild 0 40 Canarygrass 10 20 Chickweed 98 50 Deadnettle 98 100 Field Poppy 100 98 Field Violet 0 0 Foxtail, Green 0 0 Galium 50 35 Kochia 90 25 Lambsquarters 100 100 Mustard, Wild 35 — Oat, Wild 0 0 Oilseed Rape 65 40 Pigweed 85 65 Radish, Wild 0 0 Ryegrass, Italian 0 0 Wheat, Spring 0 0 Wheat, Winter 0 0 Windgrass 25 40 62 g ai/ha Preemergence Barley, Spring 0 0 Barley, Winter 0 0 Blackgrass 0 0 Bluegrass 0 20 Bromegrass, Downy 0 0 Buckwheat, Wild 0 0 Canarygrass 0 — Chickweed 98 — Deadnettle 95 90 Field Poppy 95 98 Field Violet 0 0 Foxtail, Green 0 0 Galium 0 35 Kochia 30 5 Lambsquarters 0 70 Mustard, Wild 5 5 Oat, Wild 0 0 Oilseed Rape 35 30 Pigweed 65 50 Radish, Wild 0 0 Russian Thistle 0 0 Ryegrass, Italian 0 0 Wheat, Spring 0 0 Wheat, Winter 0 0 Windgrass 25 40 31 g ai/ha Preemergence Barley, Spring 0 0 Barley, Winter 0 0 Blackgrass 0 0 Bluegrass 0 0 Bromegrass, Downy 0 0 Buckwheat, Wild 0 0 Canarygrass 0 — Chickweed 98 — Deadnettle 75 50 Field Poppy 75 80 Field Violet 0 0 Foxtail, Green 0 0 Galium — 0 Kochia 5 5 Lambsquarters 0 20 Mustard, Wild 0 — Oat, Wild 0 0 Oilseed Rape 20 20 Pigweed 20 0 Radish, Wild 0 0 Russian Thistle 0 0 Ryegrass, Italian 0 0 Wheat, Spring 0 0 Wheat, Winter 0 0 Windgrass 15 20 16 g ai/ha Preemergence Barley, Spring 0 0 Barley, Winter 0 0 Blackgrass 0 0 Bluegrass 0 0 Bromegrass, Downy 0 0 Buckwheat, Wild 0 0 Canarygrass 0 — Chickweed 75 — Deadnettle 0 35 Field Poppy — 50 Field Violet 0 0 Foxtail, Green 0 0 Galium — 0 Kochia 5 5 Lambsquarters 0 0 Mustard, Wild 0 0 Oat, Wild 0 0 Oilseed Rape 0 0 Pigweed 0 0 Radish, Wild 0 0 Russian Thistle 0 0 Ryegrass, Italian 0 0 Wheat, Spring 0 0 Wheat, Winter 0 0 Windgrass 0 20

Test D

Seeds of plant species selected from bermudagrass (Cynodon dactylon), Surinam grass (Brachiaria decumbens), large crabgrass (Digitaria sanguinalis), green foxtail (Setaria viridis), goosegrass (Eleusine indica), j ohnsongrass (Sorghum halepense), kochia (Kochia scoparia), morningglory (pitted morningglory, Ipomoea lacunosa), nutsedge (purple nutsedge, Cyperus rotundus), ragweed (common ragweed, Ambrosia elatior), black mustard (Brassica nigra), guineagrass (Panicum maximum), dallisgrass (Paspalum dilatatum), barnyardgrass (Echinochloa crus-galli), sandbur (southern sandbur, Cenchrus echinatus), sowthistle (common sowthistle, Sonchus oleraceous), prickly sida (Sida spinosa), Italian ryegrass (Lolium multiflorum), purslane (common purslane, Portulaca oleracea), signalgrass (broadleaf signalgrass, Brachiaria platyphylla), groundsel (common groundsel, Senecio vulgaris), chickweed (common chickweed, Stellaria media), dayflower (Virginia (VA) dayflower, Commelina virginica), bluegrass (annual bluegrass, Poa annua), naked crabgrass (Digitaria nuda), itchgrass (Rottboellia cochinchinensis), quackgrass (Elytrigia repens), field bindweed (Convolvulus arvensis), spanishneedles (Bidens bipinnata), mallow (common mallow, Malva sylvestris) and Russian thistle (Salsola kali), were planted into a blend of loam soil and sand and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. At the same time, plants from these weed species were treated with postemergence applications of the test chemicals formulated in the same manner. Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage) for postemergence treatments.

Treated plants and controls were maintained in a greenhouse for 14 to 21 days, after which time all species were visually evaluated and compared to controls. Plant response ratings, summarized in Table D, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.

TABLE D 250 g ai/ha Postemergence Compounds 226 235 238 240 243 244 245 Barnyardgrass 95 95 95 95 90 90 90 Bermudagrass 98 95 95 95 95 95 80 Black Mustard 85 98 98 98 98 98 98 Bluegrass 30 50 40 35 35 20 35 Chickweed 85 70 50 70 70 60 50 Crabgrass, Large 85 80 80 70 85 75 75 Crabgrass, Naked 75 — — — — — — Dallisgrass 35 80 75 75 90 80 85 Dayflower, VA 65 75 75 75 75 70 75 Field Bindweed 80 70 50 70 70 70 70 Foxtail, Green 98 98 95 98 98 100  95 Goosegrass 75 75 75 80 75 70 75 Groundsel 100  100  100  100  100  100  100  Guineagrass 80 75 75 80 85 75 85 Itchgrass 90 90 80 80 85 75 75 Johnsongrass 90 85 80 95 75 75 75 Kochia 70 85 75 70 75 65 75 Mallow 65 70 60 60 70 70 70 Morningglory 80 95 90 95 85 75 80 Nutsedge, Purple  5 40 20 20 50 35 20 Prickly Sida 75 75 65 75 80 60 70 Purslane 70 70 60 50 50 50 30 Quackgrass 35 70 40 50 75 65 65 Ragweed 98 80 75 90 75 85 75 Russian Thistle 70 60 50 35 60 65 70 Ryegrass, Italian 15 35  5 35 65 60 50 Sandbur 75 75 85 90 80 75 75 Signalgrass 65 95 65 85 95 35 75 Sowthistle 98 98 95 98 98 100  95 Spanishneedles 80 85 75 75 70 75 75 Surinam Grass 90 85 85 95 85 80 75 125 g ai/ha Postemergence Compounds 47 51 52 59 66 85 87 113 128 226 228 233 235 238 Barnyardgrass 70 70 80 75 75 70 70 80 90 95 80 85 95 85 Bermudagrass 90 85 80 80 65 90 85 80 90 95 70 70 95 95 Black Mustard 100  100  98 98 98 85 100  100  95 80 50 100  98 98 Bluegrass  0  0 35  5  0  5  0  0  0 10  5  0 35 20 Chickweed 65 70 100  — 95 100  100  — 70 35 75 60 60 40 Crabgrass, Large 65 35 70 70 35 75 75 70 70 75 75 60 75 75 Crabgrass, Naked 65 65 95 70 70 80 75 75 75 70 — 70 — — Dallisgrass 15 70 75 50 60 80 75 70 60 30  5 35 80 70 Dayflower, VA 30 20 60 — 30 80 70 60 70 — 85 60 75 70 Field Bindweed 65 60 70 60  0 75 40 — 65 70 70 70 65 — Foxtail, Green 95 65 95 35 80 65 60 90 70 80 80 35 98 80 Goosegrass 65 65 80 65 75 75 65 65 70 70 70 65 75 75 Groundsel 100  100  100  100  80 100  100  100  100  95 100  100  100  100  Guineagrass 30 50 75 20 30 60 30 70 35 80 15 50 75 65 Itchgrass 10 80 65 75 40 70 30 70 65 70 65 80 80 75 Johnsongrass 65 70 — 60 60 80 60 75 65 80 70 50 85 75 Kochia 30 20 40 50 40 60 60 50 40 70 75 35 70 65 Mallow 65 20 75 40 60 75 70 20 40 50 65  0 70 50 Morningglory 50 65 70 50 90 90 50 90 70 70 50 70 95 80 Nutsedge, Purple 20 20 40 25 30 65 50 50 50  0 15  0 30 20 Prickly Sida 90 75 90 70 98 98 95 70 80 70 65 60 70 50 Purslane 30 35 75 50 75 90 35 75 50 65 35 40 60 60 Quackgrass  5  0 20  0  5 20  5 30  5 20  5 25 40 30 Ragweed 95 85 95 80  5 100  98 80 90 90 75 98 80 75 Russian Thistle — — — 65 — — 35 20 — 40 65 10 50 50 Ryegrass, Italian 30  0 35  5 15 20  5 50  5  0  5  5  5  5 Sandbur 35 60 80 25 90 95 35 60 35 75 5 75 75 75 Signalgrass 20 50 90 20 30 75 60 75 35 65 20 35 90 60 Sowthistle 100  100  100  100  90 100  100  100  100  98 98 100  98 95 Spanishneedles 70 70 80 70 80 95 70 60 65 75 70 60 80 70 Surinam Grass 70 80 90 60 90 85 40 — 50 90 70 60 75 75 25 g ai/ha Postemergence Compounds 240 243 244 245 Barnyardgrass 95 80 85 85 Bermudagrass 95 95 95 80 Black Mustard 98 98 95 98 Bluegrass 35 35 10 35 Chickweed 60 60 40 50 Crabgrass, Large 65 85 75 75 Crabgrass, Naked — — — — Dallisgrass 75 90 75 80 Dayflower, VA 70 70 65 65 Field Bindweed 70 70 65 60 Foxtail, Green 98 90 95 95 Goosegrass 80 70 70 70 Groundsel 100  100  100  100  Guineagrass 80 75 75 75 Itchgrass 80 75 75 75 Johnsongrass 95 70 75 75 Kochia 65 70 50 70 Mallow 60 70 60 50 Morningglory 90 85 75 80 Nutsedge, Purple  5 25 10  5 Prickly Sida 75 70 40 50 Purslane — 50 50 30 Quackgrass 35 70 50 40 Ragweed 80 75 80 75 Russian Thistle — 30 60 60 Ryegrass, Italian 35 30 35 20 Sandbur 90 75 75 75 Signalgrass 75 75 25 50 Sowthistle 98 95 100  95 Spanishneedles 75 70 75 70 Surinam Grass 95 75 80 75 62 g ai/ha Postemergence Compounds 47 51 52 59 66 85 87 113 128 226 233 235 238 240 Barnyardgrass 70 70 75 60 70 65 60 80 70 85 85 80 80 95 Bermudagrass 70 80 75 70 65 80 70 80 80 95 70 95 90 95 Black Mustard 100  — 98 65 50 75 100  100  95 80 50 80 95 80 Bluegrass  0  0 35  0  0  5  0  0  0 10  0 20  5 35 Chickweed — — 98 70 35 100  75 — 65 35 — 30 35 50 Crabgrass, Large 60 35 70 50 25 75 70 70 60 75 50 75 70 65 Crabgrass, Naked 35 — 95 50 65 75 70 70 70 65 60 — — — Dallisgrass 15 30 70 20 35 65 50 60 30 20 10 75 65 70 Dayflower, VA 20 10 30 60  0 60 60 60 60 50 35 70 65 60 Field Bindweed 50 20 70 30  0 75 25 65 65 70 50 65 50 70 Foxtail, Green 50 40 85 20 65 35 35 70 65 70 30 95 80 98 Goosegrass 65 65 75 50 65 75 65 65 65 70 60 75 70 70 Groundsel 100  100  100  100  80 100  100  100  100  90 90 100  100  100  Guineagrass 20 30 75 20 10 35 20 50 30 80 40 75 50 65 Itchgrass  5 40 65 15 35 65 30 65 40 70 70 75 70 75 Johnsongrass 35 60 85 40 50 80 40 65 50 80 50 70 70 90 Kochia 20  5  0 20 25 20 35 50 30 60 30 60 50 65 Mallow 65  0 65  5 60 70 70  0 40 50  0 50 35 40 Morningglory — 20 70 50 90 75 40 90 70 70 70 75 80 80 Nutsedge, Purple 10 15 35 20 20 50 20 35 35  0  0  5 10  5 Prickly Sida 80 65 80 70 98 95 80 70 65 65 50 65 30 65 Purslane 30 35 65 35 75 90 35 50 30 50 30 60 60 35 Quackgrass  0  0 15  0  5 15  0 20  0  0 10 30  5 30 Ragweed 80 80 95 —  0 80 95 75 90 90 75 70 75 75 Russian Thistle 20 — — — — — — 20 20 — — 30 40 35 Ryegrass, Italian 20  0 15  5  0 15  0 35  0  0  5  5  5 35 Sandbur 20 25 75  5 35 65 20 60  5 75 70 75 75 70 Signalgrass 15 50 80 10 30 60 60 60 35 40 25 90 35 75 Sowthistle 100  100  98 100  70 100  98 100  100  98 — 98 95 98 Spanishneedles 65 60 80 70 80 90 60 50 50 75 50 70 70 65 Surinam Grass 60 70 80 50 90 75 40 80 30 70 50 75 75 70 62 g ai/ha Postemergence Compounds 243 244 245 Barnyardgrass 80 80 85 Bermudagrass 85 80 80 Black Mustard 75 75 95 Bluegrass  5 10 20 Chickweed 50 20 25 Crabgrass, Large 80 75 70 Crabgrass, Naked — — — Dallisgrass 80 75 75 Dayflower, VA 65 50 35 Field Bindweed 70 35 50 Foxtail, Green 85 90 90 Goosegrass 70 60 70 Groundsel 100  100  100  Guineagrass 75 75 75 Itchgrass 75 70 70 Johnsongrass 70 70 75 Kochia 60 50 65 Mallow 60 50 50 Morningglory 85 70 75 Nutsedge, Purple 25  0  5 Prickly Sida 65 35 50 Purslane 50 50  5 Quackgrass 40 40 35 Ragweed 70 70 75 Russian Thistle 30 40 60 Ryegrass, Italian 20 15  5 Sandbur 75 70 70 Signalgrass 75 20 40 Sowthistle 90 95 95 Spanishneedles 65 65 70 Surinam Grass 75 75 75 31 g ai/ha Postemergence Compounds 47 51 52 59 66 85 87 113 128 226 228 233 235 238 Barnyardgrass 70 70 75 60 65 50 50 75 70 85 20 75 80 75 Bermudagrass 50 75 75 40 50 75 65 70 70 90 70 70 80 80 Black Mustard 100  95 90 40 20 60 65 — 95 65 20 50 80 80 Bluegrass  0  0 25  0  0  0  0  0  0  0  0  0  5  0 Chickweed 65 — 90 70 — 80 75 70 — 20 35 50  5 30 Crabgrass, Large 50 35 70 35 25 60 65 60 50 65 65 40 70 50 Crabgrass, Naked 35 50 75 30 50 50 60 65 65 60 — 50 — — Dallisgrass 10 20 65 10 35 25 25 10 20 15  0 10 70 10 Dayflower, VA 15 10  5 —  0 30 35 40 50 50 35 35 60 35 Field Bindweed 40  5 70  5  0 75 15 65 50 70 65 50 60 35 Foxtail, Green 35 20 70  5 35 25 30 60 40 65 70 10 70 75 Goosegrass 65 65 75 20 50 65 35 50 40 70 50 50 75 50 Groundsel 100  98 100  90 60 100  98 90 100  80 100  50 100  100  Guineagrass 20 30 70 10  5 20 20 25 30 80  0 30 75 25 Itchgrass  5 20 50 15 15 35  0 10 40 50 40 65 70 70 Johnsongrass 15 35 75 35 20 50 30 40 40 50 65 35 70 60 Kochia 10  5  0  5 25 10 35 40 30 60 65 20 20 20 Mallow 50  0 65  5 30 65 60  0  5 35 40  0 10 25 Morningglory  5 20 65 40 70 70 40 60 65 50 50 60 75 70 Nutsedge, Purple  0  0 20  0  5 30 10 10 10  0  5  0  5  5 Prickly Sida 70 50 65 40 98 95 80 60 60 40 40 50 65 30 Purslane 20 20 65 35 50 80 25 30 30 50 — 30 60 60 Quackgrass  0  0 10  0  5  0  0  0  0  0  0  0  5  5 Ragweed 75 75 95 70  0 80 80 70 75 80 75 75 70 70 Russian Thistle — — — — — — —  0  0 — 20 — 30 30 Ryegrass, Italian 10  0  0  0  0  0  0 20  0  0  0  0  5  5 Sandbur  5 25 65  5 35 50  5 10  5 60  5 65 75 50 Signalgrass  5 35 60  5 10 35 30 40 30 35 15  5 65 20 Sowthistle 100  98 95 100  65 100  98 95 100  90 95 100  98 95 Spanishneedles 40 50 75 50 70 75 60 35 50 70 65 35 65 65 Surinam Grass 50 60 65 35 60 75 40 75 25 65  5 — 75 75 31 g ai/ha Postemergence Compounds 240 243 244 245 Barnyardgrass 80 75 80 80 Bermudagrass 85 75 80 80 Black Mustard 70 50 50 75 Bluegrass  5  5  0  5 Chickweed 25 35 15  5 Crabgrass, Large 40 75 70 70 Crabgrass, Naked — — — — Dallisgrass  5 75 40 65 Dayflower, VA 35 35 30 20 Field Bindweed 60 65 20 50 Foxtail, Green 95 80 75 85 Goosegrass 70 65 50 70 Groundsel 100  98 100  95 Guineagrass 40 70 70 75 Itchgrass 75 75 60 70 Johnsongrass 70 70 70 70 Kochia 20 50 25 50 Mallow 10 50 50 35 Morningglory 65 75 65 70 Nutsedge, Purple  0 20  0  5 Prickly Sida 35 60 25 30 Purslane  0 35 25  0 Quackgrass 25 35 20 20 Ragweed 70 65 65 70 Russian Thistle 35 20 20 25 Ryegrass, Italian  0  0  5  5 Sandbur 70 75 70 65 Signalgrass 20 50 20 10 Sowthistle 98 90 75 95 Spanishneedles 65 60 65 65 Surinam Grass 70 75 75 75 16 g ai/ha Postemergence Compounds 47 51 52 59 66 85 87 113 128 233 Barnyardgrass 70 65 75 40 35 30 35 65 35 65 Bermudagrass 50 65 75 35 5 65 65 65 70 70 Black Mustard 95 70 65 10  0 35 40 100  95 20 Bluegrass  0  0 15  0  0  0  0  0  0  0 Chickweed 50 — 75 — — — 75 — 60 — Crabgrass, Large 20 25 65 35 20 60 40 60 40 20 Crabgrass, Naked 20 35 70 20 — — 50 50 35 30 Dallisgrass  5 20 60 10 35 15 25 10 10  0 Dayflower, VA 10 10  5 25  0 20 10 20 50 15 Field Bindweed 35  5 50  5  0 65  0 50 50 10 Foxtail, Green  5 10 70  0 20 20  5 25 25  5 Goosegrass 40 35 65 20 50 40 30 40 35 40 Groundsel 100  85 100  70 — 100  98 90 100  30 Guineagrass 10 20 50 10  5 10 10 25 20 20 Itchgrass  0  0 25  0 10 30  0  0  0 50 Johnsongrass  5 20 65 30  0 35 20 40 35 20 Kochia  0  5  0  5 —  0 25 25 20 10 Mallow 35  0 50  0 25 60 40  0  5  0 Morningglory  5  0 50  0 65 70 40 50 65 50 Nutsedge, Purple  0  0  0  0  0  5  0  0  0  0 Prickly Sida 60 50 65 40 — — 70 50 50 30 Purslane 20 10 65 35 — 75 10 30 30 30 Quackgrass  0  0  5  0  0  0  0  0  0  0 Ragweed 75 60 90 70  0 80 70 70 — 65 Russian Thistle 20  0 — — — — —  0  0  0 Ryegrass, Italian  0  0  0  0  0  0  0  0  0  0 Sandbur  5  5 65  5 — 10  5  5  5 30 Signalgrass  0  5 50  5  0 20 20  5  0  0 Sowthistle 90 95 80 70 35 100  90 90 100  90 Spanishneedles 35 35 75 30 65 75 60 35 35 35 Surinam Grass 35 50 — 30 — — 30 60 — 30 250 g ai/ha Preemergence Compound 243 Barnyardgrass 100 Bermudagrass 100 Black Mustard 100 Bluegrass 100 Crabgrass, Large 100 Crabgrass, Naked 100 Dallisgrass 100 Dayflower, VA 100 Field Bindweed 100 Foxtail, Green 100 Goosegrass 100 Guineagrass 100 Itchgrass 100 Johnsongrass 100 Kochia 100 Mallow 98 Morningglory 100 Nutsedge, Purple 100 Prickly Sida 100 Purslane 100 Quackgrass 98 Ragweed 100 Russian Thistle 100 Ryegrass, Italian 100 Sandbur 100 Signalgrass 100 Spanishneedles 100 Surinam Grass 100 Compounds 47 51 52 59 66 85 87 113 128 233 243 125 g ai/ha Preemergence Barnyardgrass  5 10 10 10 75 98 95 35 15 40 100  Bermudagrass 100  30 100  90  5 100  98 85 75 85 100  Black Mustard 100  100  100  100  80 100  100  100  95 65 100  Bluegrass 35  0 20 30  0 15 35  0 25 40 95 Chickweed — — 95 — 98 100  — — — — — Crabgrass, Large 95  5 98 65 98 100  100  95 — 90 100  Crabgrass, Naked 98  0 80 95 25 98 100  100  75 65 100  Dallisgrass 75 90 95 75 95 98 98 100  98 35 100  Dayflower, VA 50  0 40 35  5 95 65 65 25 100  100  Field Bindweed 35  0 50 60 20 98 70 90 98 85 100  Foxtail, Green  0  0 15  0  5 70 10 20  0  0 100  Goosegrass 75 40 98 80 50 98 100  95 90 100  100  Guineagrass  0 75 —  0 65 75 75 100   0  0 100  Itchgrass  0  0  5 20  0 50 20  0 20 20 50 Johnsongrass 75 70 95 35 30 95 70 10 65 65 100  Kochia 100  50 35  0 90 95 100  100  50 80 100  Mallow 98 65 — 65 75 98 100  90 100  60 80 Morningglory 65 100  100  80 95 100  95 90 90 95 98 Nutsedge, Purple 35  5 40 80 70 95 75 80 70  5 100  Prickly Sida 100  35 100  65 90 100  100  90 30 70 100  Purslane 100  100  100  100  100  100  100  100  100  100  100  Quackgrass  0  0 20  0  0 20  0  0  0  0 85 Ragweed 100  95 98 100   0 100  98 98 100  98 100  Russian Thistle 100  75 — 100  — — 100  100  100  100  100  Ryegrass, Italian  0  0 15 20  0 20 30 20  0 20 98 Sandbur 90 75 98  0 80 98 95 90 20 85 100  Signalgrass 90 10 90  5  5 95 75 90  5 35 95 Sowthistle 100  100  100  100   0 100  100  100  100  100  — Spanishneedles 95 98 98 90 95 100  98 95 100  95 100  Surinam Grass — — 98 100  98 100  100  95 90 100  100  62 g ai/ha Preemergence Barnyardgrass  5  0  0  0  5 95 50  0  5  5 100  Bermudagrass 50  0 90 40  5 100  98 70 65 85 100  Black Mustard 80 75 80 60 35 98 100  80 85 20 100  Bluegrass  0  0  0 15  0  0 25  0 25 25 40 Chickweed — — — — 90 100  — — — — — Crabgrass, Large  5  5 75 35 50 100  95 95 60 25 100  Crabgrass, Naked 60  0 20 65 10 95 100  90  0 65 100  Dallisgrass 65 10 50 65  5 95 80 50 65  0 100  Dayflower, VA 50 —  0 35  0 90 65 50 10 100  100  Field Bindweed  0  0 20 20  0 70 40 65 35 85 100  Foxtail, Green  0  0  0  0  0 40  0  0  0  0 35 Goosegrass  5 40 80 20 30 75 95 75 65 98 100  Guineagrass  0  0 50  0  0 70 50 100   0  0 100  Itchgrass  0  0  0  0  0 35 20  0  0  0 25 Johnsongrass  0 20 75 10  0 80 20 10 15 20 100  Kochia 100   0 25  0 65 75 100  100  50 20 80 Mallow 65  0 — 65  5 95 80  5 70  0 50 Morningglory 20 30  0  0 90 90 80 60 0 95 — Nutsedge, Purple 10  5 30 20 35 95 50 20  0  0 20 Prickly Sida 65 20 50  5  5 100  100  70 25  0 100  Purslane 95 65 90 100  60 100  100  100  100  100  95 Quackgrass  0  0  0  0  0 15  0  0  0  0 35 Ragweed 100  65 70 90  0 100  98 80 90 95 100  Russian Thistle 50 75 — 90 — — 90 100  95 75 100  Ryegrass, Italian  0  0  0  0  0 10  0  0  0  0 60 Sandbur  5  5  5  0 10 60 50 65 20 50 100  Signalgrass 10  0 50  0  5 75 75  0  0 10 75 Sowthistle 100  98 80 100   0 100  100  100  100  100  — Spanishneedles 95 90 95  0 85 98 85 — 90 85 100  Surinam Grass  0 100  98 100  95 100  95 — 80 65 100  31 g ai/ha Preemergence Barnyardgrass  0  0  0  0  0 75  5  0  0  0 60 Bermudagrass 25  0 70  0  0 100  65 50  0  5 75 Black Mustard 65 50 20 40  5 60 75  0 60  0 80 Bluegrass  0  0  0  0  0  0 20  0  0  0 10 Chickweed — — — — 20 100  — — — — — Crabgrass, Large  0  5 20 35 30 98 75 30 25  5 100  Crabgrass, Naked  0  0  0  0  0 95 80  0  0  0 100  Dallisgrass 25 10 10  0  5 80 50 50 20  0 75 Dayflower, VA 35  0  0  0  0 10  0 50  0 80 90 Field Bindweed  0  0 —  0  0 70  0 20  0  0 100  Foxtail, Green  0  0  0  0  0  5  0  0  0  0 20 Goosegrass  0 20 60  5  0 75 35 25  5 95 100  Guineagrass  0  0 —  0  0 10  0 65  0  0 100  Itchgrass  0  0  0  0  0 15 20  0  0  0 10 Johnsongrass  0  0  0  0  0 65  5  0  0  0 95 Kochia 50 — 25  0 65 20 98 70  0  0 — Mallow  0  0 — 65  0 — —  5 70  0  0 Morningglory  0  0  0  0  0 70 — 60  0 80 90 Nutsedge, Purple  0  0  5 20  0 75  5 10  0  0  5 Prickly Sida 50 20  0  0  0 100  60 35  0  0 85 Purslane  0 50 60 100   0 100  100  100   0  0 75 Quackgrass  0  0  0  0  0  0  0  0  0  0  0 Ragweed 50 50 50 50  0 95 98 50 75 70 100  Russian Thistle — — — 90 — — 75 65  0 65 100  Ryegrass, Italian  0  0  0  0  0  0  0  0  0  0 50 Sandbur  0  0  0  0  5  5 25  0  0  0 75 Signalgrass  0  0  0  0  5 60  0  0  0  0 — Sowthistle 65 75 80 95  0 100  100  75 80 50 — Spanishneedles 95  0 70  0 60 98 65  0  0 50 100  Surinam Grass — 98 98 90 80 100  50 40 35  5 100  16 g ai/ha Preemergence Compounds 47 51 52 59 66 85 87 113 128 233 Barnyardgrass 0 0 0 0 0 60  0 0 0 0 Bermudagrass 10  0 30  0 0 80  65  50  0 5 Black Mustard 0 0 0 20  0 50  75  0 60  0 Bluegrass 0 0 0 0 0 0 20  0 0 0 Chickweed — — — — 0 90  — — — — Crabgrass, Large 0 0 0 0 15  95  50  20  0 0 Crabgrass, Naked 0 0 0 0 0 0 — 0 0 0 Dallisgrass 0 0 5 0 0 50  50  5 0 0 Dayflower, VA 35  0 0 — 0 5 0 50  — 0 Field Bindweed 0 0 20  0 0 50  0 0 0 0 Foxtail, Green 0 0 0 0 0 0 0 0 0 0 Goosegrass 0 20  5 0 0 65  35  25  0 70  Guineagrass 0 0 0 0 0 0 0 0 0 0 Itchgrass 0 0 0 0 0 10  0 0 0 0 Johnsongrass 0 0 0 0 0 50  0 0 0 0 Kochia 0 0 — 0 0 5 65  — 0 0 Mallow 0 0 — 0 0 80  — 0 — 0 Morningglory 0 0 0 0 0 — 10  60  — 0 Nutsedge, Purple 0 0 0 0 0 70  0 0 0 0 Prickly Sida 0 0 0 0 0 90  50  0 0 0 Purslane 0 0 0 65  0 80  70  90  0 0 Quackgrass 0 0 0 0 0 0 0 0 0 0 Ragweed 0 35  30  0 0 90  30  0 0 50  Russian Thistle 0 — 0 — — — 50  0 — 50  Ryegrass, Italian 0 0 0 0 0 0 0 0 0 0 Sandbur 0 0 0 0 0 5 0 0 0 0 Signalgrass 0 0 0 0 0 5 0 0 0 0 Sowthistle 65  40  0 0 0 100  98  50  80  0 Spanishneedles 0 0 35  0 0 90  0 0 0 0 Surinam Grass 0 90  0 5 0 98  0 — 0 0

Test E

Three plastic pots (ca. 16-cm diameter) for each application were partially filled with sterilized Tama silt loam soil comprising a 35:50:15 ratio of sand, silt and clay and 2.6% organic matter. Separate plantings for each of the three pots were as follows. Seeds from the U.S. of ducksalad (Heteranthera limosa), sedge (smallflower umbrella sedge, Cyperus difformis), ricefield bulrush (Scirpus mucronatus) and redstem (purple redstem, Ammannia coccinea), were planted into one 16-cm pot for each rate. Seeds from the U.S. of flatsedge (rice flatsedge, Cyperus iria), sprangletop (bearded (i.e. Brdd.) sprangletop, Leptochloa fascicularis), one stand of 9 or 10 water seeded rice seedlings (Oryza sativa cv. ‘Japonica-M202’), and two stands of 3 or 4 transplanted rice seedlings (Oryza sativa cv. ‘Japonica-M202’) were planted into one 16-cm pot for each rate. Seeds from the U.S. of barnyardgrass (Echinochloa crus-galli), late watergrass (Echinochloa oryzicola), early watergrass (Echinochloa oryzoides) and junglerice (Echinochloa colona) were planted into one 16-cm pot for each rate. Plantings were sequential so that crop and weed species were at the 2.0 to 2.5-leaf stage at time of treatment.

Potted plants were grown in a greenhouse with day/night temperature settings of 30/27° C., and supplemental balanced lighting was provided to maintain a 16-hour photoperiod. Test pots were maintained in the greenhouse until test completion.

At time of treatment, test pots were flooded to 3 cm above the soil surface, treated by application of test compounds directly to the paddy water, and then maintained at that water depth for the duration of the test. Effects of treatments on rice and weeds were visually evaluated by comparison to untreated controls after 21 days. Plant response ratings, summarized in Table E, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.

TABLE E 500 g ai/ha Flood Compounds 4 19 Barnyardgrass 60 85 Bulrush, Ricefield 80 75 Ducksalad 100 100 Flatsedge, Rice 90 100 Junglerice 50 80 Redstem 85 85 Rice, Transplanted 15 65 Rice, Water Seeded 50 95 Sedge, Umbrella 100 100 Sprangletop, Brdd. — 100 Watergrass, Early 65 85 Watergrass, Late 60 55 Compounds 4 19 28 218 250 g ai/ha Flood Barnyardgrass 60 70 0 95 Bulrush, Ricefield 80 70 65 100 Ducksalad 100 100 100 100 Flatsedge, Rice 40 95 45 75 Junglerice 25 65 0 100 Redstem 80 90 90 80 Rice, Transplanted 0 40 15 10 Rice, Water Seeded 20 70 85 35 Sedge, Umbrella 95 100 100 100 Sprangletop, Brdd. — 100 — 95 Watergrass, Early 60 65 20 60 Watergrass, Late 15 60 0 70 125 g ai/ha Flood Barnyardgrass 0 60 0 30 Bulrush, Ricefield 40 70 35 90 Ducksalad 90 95 80 95 Flatsedge, Rice 0 40 0 70 Junglerice 0 50 0 65 Redstem 80 90 50 75 Rice, Transplanted 0 35 15 0 Rice, Water Seeded 10 40 65 20 Sedge, Umbrella 90 100 90 100 Sprangletop, Brdd. — 95 — 70 Watergrass, Early 0 45 0 20 Watergrass, Late 0 45 0 40 64 g ai/ha Flood Compounds 19 28 218 Barnyardgrass 60 0 0 Bulrush, Ricefield 50 30 80 Ducksalad 85 0 85 Flatsedge, Rice 40 0 70 Junglerice 0 0 0 Redstem 0 40 65 Rice, Transplanted 0 15 0 Rice, Water Seeded 0 60 0 Sedge, Umbrella 90 85 95 Sprangletop, Brdd. 75 — 70 Watergrass, Early 20 0 20 Watergrass, Late 0 0 40 32 g ai/ha Flood Compounds 28 218 Barnyardgrass 0 0 Bulrush, Ricefield 20 80 Ducksalad 0 80 Flatsedge, Rice 0 75 Junglerice 0 0 Redstem 0 65 Rice, Transplanted 0 0 Rice, Water Seeded 45 15 Sedge, Umbrella 0 85 Sprangletop, Brdd. — 65 Watergrass, Early 0 0 Watergrass, Late 0 20

Test F

Test F evaluated the effect of combining compound 2 with bromoxynil. The test species for this experiment was Russian thistle (Salsola iberica), which was prepared by sowing seeds into a blend of loam soil and sand. Test chemicals were formulated in a non-phytotoxic solvent mixture that included a surfactant and applied postemergence to plants ranging in height from 12 to 20 cm.

Plants were grown in a greenhouse using supplemental lighting to maintain a photoperiod of 16 hours; day and night temperatures ranged between 24-30° C. and 19-21° C., respectively. Treatments consisted of Compound 2, bromoxynil, or their combination, using a spray volume of 457 L/ha. Each treatment was replicated three times. Treated plants and untreated controls were maintained in a greenhouse for 15 days, after which time all plants were visually evaluated and compared to the untreated controls. Plant responses were calculated as the mean of the three replicates and summarized in Table F. Visual evaluations were based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. Colby's Equation was used to determine the herbicidal effects expected from the mixtures. Colby's Equation (Colby, S. R. “Calculating Synergistic and Antagonistic Responses of Herbicide Combinations,” Weeds, 15(1), pp 20-22 (1967)) calculates the expected additive effect of herbicidal mixtures, and for two active ingredients is of the form:

P _(a+b) =P _(a) +P _(b)−(P _(a) P _(b)/100)

wherein P_(a+b) is the percentage effect of the mixture expected from additive contribution of the individual components:

-   -   P_(a) is the observed percentage effect of the first active         ingredient at the same use rate as in the mixture, and     -   P_(b) is the observed percentage effect of the second active         ingredient at the same use rate as in the mixture.         The results and additive effects expected from Colby's Equation         are listed in Table F1.

TABLE F1 Observed and Expected Results from Compound 2, Bromoxynil, or their combination. Postemergence Application Rate (g a.i./ha)* Russian Thistle Cmpd 2 Bromoxynil Obsd. Exp. 62 — 42 — 125 — 52 — — 70 8 — — 140 13 — 62 70 93 47 125 140 95 58 *Application rates are grams of active ingredient per hectare (g a.i./ha). “Obsd.” is observed effect. “Exp.” is expected effect calculated from Colby's Equation.

The results in Table D1 suggest the combination of Compound 2 and bromoxynil have a synergistic action based on the observed injury being greater than the expected values as calculated by the Colby Equation for an additive effect. 

What is claimed is: 1.-18. (canceled)
 19. A compound of Formula 1R (including all stereoisomers), N-oxides, and salts thereof:

wherein R¹ is phenyl, —W¹(phenyl), —W¹(S-phenyl), —W¹(SO₂-phenyl), —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each optionally substituted on ring members with up to five substituents selected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈ cycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₃-C₁₀ alkoxyalkenyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ alkoxycycloalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl or C₂-C₈ alkylsulfonylalkyl; W¹ is C₁-C₆ alkylene, C₂-C₆ alkenylene or C₂-C₆ alkynylene; W² is C₁-C₆ alkylene; R² is phenyl or —W³(phenyl), each substituted on ring members with up to two substituents selected from R²¹; or -G or; or C₁-C₆ alkyl or C₃-C₈ cycloalkyl; W³ is C₁-C₆ alkylene, C₁-C₆ alkenylene or C₁-C₆ alkynylene; each G is independently a 5- or 6-membered heterocyclic ring or an 8-, 9- or 10-membered fused bicyclic ring system, each ring or ring system optionally substituted with up to five substituents selected from R²¹ on carbon ring members and R²² on nitrogen ring members; each R²¹ is independently halogen, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH₂, —C(═S)NH₂, —C(═O)NHCN, —C(═O)NHOH, —SH, —SO₂NH₂, —SO₂NHCN, —SO₂NHOH, —OCN, —SCN, —SF₅, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈ alkoxyhaloalkyl, C₂-C₅ cyanoalkyl, C₁-C₆ hydroxyalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy, C₂-C₈ alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₁-C₆ alkylamino, C₂-C₈ dialkylamino, C₁-C₆ haloalkylamino, C₂-C₈ halodialkylamino or C₃-C₈ cycloalkylamino; and each R²² is independently C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl or C₂-C₈ alkoxyalkyl.
 20. A compound of Formula 1S (including all stereoisomers), N-oxides, and salts thereof:

wherein R¹ is phenyl, —W¹(phenyl), —W¹(S-phenyl), —W¹(SO₂-phenyl), —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each optionally substituted on ring members with up to five substituents selected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈ cycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₃-C₁₀ alkoxyalkenyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ alkoxycycloalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl or C₂-C₈ alkylsulfonylalkyl; W¹ is C₁-C₆ alkylene, C₂-C₆ alkenylene or C₂-C₆ alkynylene; W² is C₁-C₆ alkylene; R² is phenyl or —W³(phenyl), each substituted on ring members with up to two substituents selected from R²¹; or -G; or C₁-C₆ alkyl or C₃-C₈ cycloalkyl; W³ is C₁-C₆ alkylene, C₂-C₆ alkenylene or C₂-C₆ alkynylene; each G is independently a 5- or 6-membered heterocyclic ring or an 8-, 9- or 10-membered fused bicyclic ring system, each ring or ring system optionally substituted with up to five substituents selected from R²¹ on carbon ring members and R²² on nitrogen ring members; each R²¹ is independently halogen, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH₂, —C(═S)NH₂, —C(═O)NHCN, —C(═O)NHOH, —SH, —SO₂NH₂, —SO₂NHCN, —SO₂NHOH, —OCN, —SCN, —SF₅, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈ alkoxyhaloalkyl, C₂-C₅ cyanoalkyl, C₁-C₆ hydroxyalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy, C₂-C₈ alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₁-C₆ alkylamino, C₂-C₈ dialkylamino, C₁-C₆ haloalkylamino, C₂-C₈ halodialkylamino or C₃-C₈ cycloalkylamino; each R²² is independently C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl or C₂-C₈ alkoxyalkyl; and R²³ is C₁-C₁₆ alkyl; or phenyl or benzyl optionally substituted with halogen, nitro, cyano or hydroxy on ring members. 